Methyl (2E)-2-{[(2-methyl-quinolin-8-yl)-oxy]meth-yl}-3-(thio-phen-2-yl)acrylate.

In the mol-ecule of the title compound, C(19)H(17)NO(3)S, the dihedral angle formed by the quinoline ring system and the thio-phene ring is 83.15 (8)°. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into a C(8) chain running along the b axis. The packing of the mol-ecules is further influenced by C-H⋯π inter-actions.

Related literature

For the biological activity of thienyl acrylate and thio­phene derivatives, see: Anand et al. (2011 ▶); Ferreira et al. (2006 ▶); Bonini et al. (2005 ▶). For general background to quinoline derivatives, see: Mali et al. (2010 ▶). For a related structure, see: Prasath et al. (2011 ▶).

Experimental

Crystal data

C19H17NO3S

M = 339.40

Orthorhombic,

a = 24.545 (8) Å

b = 8.689 (3) Å

c = 15.809 (5) Å

V = 3371.5 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.25 × 0.23 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.949, T max = 0.959

17529 measured reflections

4152 independent reflections

2805 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.122

S = 1.03

4152 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812014560/bt5861sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014560/bt5861Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014560/bt5861Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H17NO3S	F(000) = 1424
Mr = 339.40	Dx = 1.337 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2025 reflections
a = 24.545 (8) Å	θ = 1.7–28.3°
b = 8.689 (3) Å	µ = 0.21 mm−1
c = 15.809 (5) Å	T = 293 K
V = 3371.5 (19) Å3	Block, colourless
Z = 8	0.25 × 0.23 × 0.2 mm

Bruker SMART APEXII area-detector diffractometer	4152 independent reflections
Radiation source: fine-focus sealed tube	2805 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω and φ scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −32→32
Tmin = 0.949, Tmax = 0.959	k = −11→9
17529 measured reflections	l = −20→20

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0611P)2 + 0.3929P] where P = (Fo2 + 2Fc2)/3
4152 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.66864 (5)	0.24488 (16)	0.06658 (11)	0.0385 (4)
C2	0.71433 (6)	0.15068 (18)	0.08567 (13)	0.0498 (5)
C3	0.74634 (7)	0.1053 (2)	0.01550 (16)	0.0656 (6)
H3	0.7770	0.0443	0.0240	0.079*
C4	0.73280 (7)	0.1497 (2)	−0.06405 (16)	0.0643 (6)
H4	0.7541	0.1193	−0.1098	0.077*
C5	0.68630 (6)	0.2421 (2)	−0.07710 (12)	0.0516 (4)
C6	0.66978 (9)	0.2936 (3)	−0.16408 (14)	0.0752 (6)
H6A	0.6315	0.2762	−0.1717	0.113*
H6B	0.6898	0.2362	−0.2056	0.113*
H6C	0.6775	0.4013	−0.1705	0.113*
C7	0.72541 (7)	0.1091 (2)	0.17010 (15)	0.0628 (5)
H7	0.7554	0.0475	0.1824	0.075*
C8	0.69243 (7)	0.1587 (2)	0.23369 (14)	0.0579 (5)
H8	0.7001	0.1303	0.2891	0.070*
C9	0.64683 (6)	0.25249 (19)	0.21687 (11)	0.0471 (4)
H9	0.6248	0.2858	0.2611	0.056*
C10	0.63489 (6)	0.29474 (17)	0.13523 (11)	0.0378 (4)
C11	0.55580 (6)	0.43432 (17)	0.17728 (10)	0.0385 (3)
H11A	0.5761	0.4878	0.2210	0.046*
H11B	0.5378	0.3464	0.2027	0.046*
C12	0.51445 (6)	0.54034 (17)	0.13842 (10)	0.0383 (3)
C13	0.46895 (6)	0.49681 (18)	0.09823 (10)	0.0396 (4)
H13	0.4484	0.5781	0.0771	0.048*
C14	0.44592 (6)	0.34661 (17)	0.08167 (11)	0.0415 (4)
C15	0.39555 (7)	0.32582 (19)	0.04619 (13)	0.0517 (4)
H15	0.3733	0.4066	0.0290	0.062*
C16	0.38082 (8)	0.1701 (2)	0.03840 (15)	0.0622 (5)
H16	0.3477	0.1372	0.0162	0.075*
C17	0.41989 (7)	0.0735 (2)	0.06666 (13)	0.0604 (5)
H17	0.4169	−0.0332	0.0660	0.072*
C18	0.52379 (6)	0.70908 (19)	0.14450 (12)	0.0453 (4)
C19	0.58520 (9)	0.9061 (2)	0.18099 (16)	0.0772 (7)
H19A	0.5752	0.9586	0.1299	0.116*
H19B	0.6234	0.9199	0.1914	0.116*
H19C	0.5648	0.9475	0.2275	0.116*
N1	0.65531 (5)	0.28865 (15)	−0.01364 (9)	0.0434 (3)
O1	0.59204 (4)	0.38425 (13)	0.11118 (7)	0.0437 (3)
O2	0.57341 (5)	0.74353 (13)	0.17233 (9)	0.0614 (4)
O3	0.49055 (6)	0.80581 (14)	0.12741 (11)	0.0718 (5)
S1	0.475215 (18)	0.16968 (5)	0.10362 (3)	0.05398 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0292 (6)	0.0331 (7)	0.0532 (10)	−0.0013 (5)	−0.0009 (6)	−0.0032 (7)
C2	0.0326 (7)	0.0414 (8)	0.0753 (14)	0.0045 (6)	−0.0021 (8)	−0.0043 (9)
C3	0.0393 (9)	0.0571 (11)	0.1005 (18)	0.0135 (8)	0.0081 (10)	−0.0103 (12)
C4	0.0466 (10)	0.0657 (12)	0.0806 (16)	0.0037 (8)	0.0205 (10)	−0.0188 (12)
C5	0.0426 (8)	0.0529 (10)	0.0594 (12)	−0.0063 (7)	0.0110 (8)	−0.0130 (9)
C6	0.0673 (13)	0.1046 (17)	0.0536 (13)	0.0006 (12)	0.0134 (10)	−0.0128 (13)
C7	0.0435 (9)	0.0585 (10)	0.0864 (16)	0.0137 (8)	−0.0141 (10)	0.0079 (11)
C8	0.0513 (10)	0.0604 (11)	0.0621 (13)	0.0059 (8)	−0.0169 (9)	0.0089 (10)
C9	0.0440 (8)	0.0479 (9)	0.0493 (11)	0.0032 (7)	−0.0048 (7)	0.0027 (9)
C10	0.0319 (7)	0.0341 (7)	0.0475 (10)	0.0012 (5)	−0.0021 (6)	0.0019 (7)
C11	0.0370 (7)	0.0404 (8)	0.0380 (9)	0.0048 (6)	0.0042 (6)	0.0013 (7)
C12	0.0371 (8)	0.0386 (7)	0.0392 (9)	0.0065 (6)	0.0076 (6)	0.0014 (7)
C13	0.0375 (7)	0.0377 (7)	0.0437 (10)	0.0074 (6)	0.0064 (7)	0.0049 (7)
C14	0.0401 (8)	0.0394 (8)	0.0448 (10)	0.0059 (6)	0.0013 (7)	0.0045 (7)
C15	0.0451 (9)	0.0466 (9)	0.0634 (13)	0.0031 (7)	−0.0078 (8)	0.0060 (9)
C16	0.0514 (10)	0.0573 (11)	0.0778 (15)	−0.0074 (8)	−0.0133 (10)	0.0012 (10)
C17	0.0643 (11)	0.0429 (9)	0.0740 (14)	−0.0046 (8)	−0.0061 (10)	0.0021 (10)
C18	0.0462 (9)	0.0416 (8)	0.0479 (11)	0.0053 (7)	0.0016 (7)	0.0007 (8)
C19	0.0833 (15)	0.0476 (11)	0.1007 (19)	−0.0120 (9)	−0.0250 (13)	−0.0013 (12)
N1	0.0353 (6)	0.0454 (7)	0.0496 (9)	−0.0011 (5)	0.0047 (6)	−0.0049 (7)
O1	0.0397 (6)	0.0511 (6)	0.0403 (7)	0.0156 (5)	0.0053 (4)	0.0047 (5)
O2	0.0562 (7)	0.0449 (7)	0.0830 (10)	−0.0036 (5)	−0.0169 (6)	−0.0003 (7)
O3	0.0635 (8)	0.0401 (6)	0.1119 (14)	0.0101 (6)	−0.0197 (8)	−0.0007 (7)
S1	0.0524 (3)	0.0389 (2)	0.0707 (4)	0.00640 (17)	−0.0103 (2)	0.0031 (2)

C1—N1	1.364 (2)	C11—C12	1.502 (2)
C1—C2	1.421 (2)	C11—H11A	0.9700
C1—C10	1.432 (2)	C11—H11B	0.9700
C2—C7	1.409 (3)	C12—C13	1.339 (2)
C2—C3	1.416 (3)	C12—C18	1.487 (2)
C3—C4	1.357 (3)	C13—C14	1.446 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.411 (3)	C14—C15	1.370 (2)
C4—H4	0.9300	C14—S1	1.7323 (16)
C5—N1	1.322 (2)	C15—C16	1.406 (2)
C5—C6	1.502 (3)	C15—H15	0.9300
C6—H6A	0.9600	C16—C17	1.351 (3)
C6—H6B	0.9600	C16—H16	0.9300
C6—H6C	0.9600	C17—S1	1.6983 (19)
C7—C8	1.361 (3)	C17—H17	0.9300
C7—H7	0.9300	C18—O3	1.2021 (19)
C8—C9	1.410 (2)	C18—O2	1.3292 (19)
C8—H8	0.9300	C19—O2	1.448 (2)
C9—C10	1.373 (2)	C19—H19A	0.9600
C9—H9	0.9300	C19—H19B	0.9600
C10—O1	1.3622 (17)	C19—H19C	0.9600
C11—O1	1.4396 (17)
N1—C1—C2	123.20 (15)	C12—C11—H11A	110.1
N1—C1—C10	118.78 (13)	O1—C11—H11B	110.1
C2—C1—C10	118.01 (16)	C12—C11—H11B	110.1
C7—C2—C3	124.31 (17)	H11A—C11—H11B	108.5
C7—C2—C1	120.08 (17)	C13—C12—C18	115.95 (14)
C3—C2—C1	115.61 (18)	C13—C12—C11	125.75 (14)
C4—C3—C2	120.75 (17)	C18—C12—C11	118.30 (13)
C4—C3—H3	119.6	C12—C13—C14	131.81 (14)
C2—C3—H3	119.6	C12—C13—H13	114.1
C3—C4—C5	119.70 (18)	C14—C13—H13	114.1
C3—C4—H4	120.1	C15—C14—C13	123.10 (14)
C5—C4—H4	120.1	C15—C14—S1	109.86 (12)
N1—C5—C4	121.90 (19)	C13—C14—S1	127.04 (12)
N1—C5—C6	116.64 (17)	C14—C15—C16	113.27 (15)
C4—C5—C6	121.46 (18)	C14—C15—H15	123.4
C5—C6—H6A	109.5	C16—C15—H15	123.4
C5—C6—H6B	109.5	C17—C16—C15	112.75 (16)
H6A—C6—H6B	109.5	C17—C16—H16	123.6
C5—C6—H6C	109.5	C15—C16—H16	123.6
H6A—C6—H6C	109.5	C16—C17—S1	112.05 (14)
H6B—C6—H6C	109.5	C16—C17—H17	124.0
C8—C7—C2	120.25 (16)	S1—C17—H17	124.0
C8—C7—H7	119.9	O3—C18—O2	122.61 (16)
C2—C7—H7	119.9	O3—C18—C12	124.76 (15)
C7—C8—C9	121.07 (18)	O2—C18—C12	112.62 (13)
C7—C8—H8	119.5	O2—C19—H19A	109.5
C9—C8—H8	119.5	O2—C19—H19B	109.5
C10—C9—C8	120.07 (17)	H19A—C19—H19B	109.5
C10—C9—H9	120.0	O2—C19—H19C	109.5
C8—C9—H9	120.0	H19A—C19—H19C	109.5
O1—C10—C9	125.42 (14)	H19B—C19—H19C	109.5
O1—C10—C1	114.06 (14)	C5—N1—C1	118.84 (14)
C9—C10—C1	120.52 (14)	C10—O1—C11	116.56 (12)
O1—C11—C12	107.82 (12)	C18—O2—C19	115.72 (14)
O1—C11—H11A	110.1	C17—S1—C14	92.07 (8)
N1—C1—C2—C7	−179.55 (15)	C12—C13—C14—C15	173.31 (18)
C10—C1—C2—C7	−0.1 (2)	C12—C13—C14—S1	−5.6 (3)
N1—C1—C2—C3	0.7 (2)	C13—C14—C15—C16	−178.11 (17)
C10—C1—C2—C3	−179.79 (14)	S1—C14—C15—C16	1.0 (2)
C7—C2—C3—C4	179.71 (18)	C14—C15—C16—C17	−0.8 (3)
C1—C2—C3—C4	−0.6 (3)	C15—C16—C17—S1	0.2 (3)
C2—C3—C4—C5	0.0 (3)	C13—C12—C18—O3	11.2 (3)
C3—C4—C5—N1	0.6 (3)	C11—C12—C18—O3	−168.58 (18)
C3—C4—C5—C6	−179.88 (19)	C13—C12—C18—O2	−169.61 (15)
C3—C2—C7—C8	179.74 (17)	C11—C12—C18—O2	10.6 (2)
C1—C2—C7—C8	0.1 (3)	C4—C5—N1—C1	−0.4 (2)
C2—C7—C8—C9	−0.2 (3)	C6—C5—N1—C1	179.99 (15)
C7—C8—C9—C10	0.3 (3)	C2—C1—N1—C5	−0.2 (2)
C8—C9—C10—O1	179.81 (15)	C10—C1—N1—C5	−179.71 (13)
C8—C9—C10—C1	−0.3 (2)	C9—C10—O1—C11	−1.8 (2)
N1—C1—C10—O1	−0.41 (19)	C1—C10—O1—C11	178.33 (12)
C2—C1—C10—O1	−179.90 (13)	C12—C11—O1—C10	175.71 (12)
N1—C1—C10—C9	179.70 (14)	O3—C18—O2—C19	0.0 (3)
C2—C1—C10—C9	0.2 (2)	C12—C18—O2—C19	−179.19 (17)
O1—C11—C12—C13	83.08 (19)	C16—C17—S1—C14	0.28 (18)
O1—C11—C12—C18	−97.16 (16)	C15—C14—S1—C17	−0.72 (15)
C18—C12—C13—C14	−178.52 (16)	C13—C14—S1—C17	178.33 (16)
C11—C12—C13—C14	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19B···Cg3i	0.96	2.89	3.505 (2)	123
C17—H17···O3ii	0.93	2.48	3.056 (2)	120

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1/C2/C7–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19B⋯Cg3i	0.96	2.89	3.505 (2)	123
C17—H17⋯O3ii	0.93	2.48	3.056 (2)	120

Symmetry codes: (i) ; (ii) .