Crystal structure of diethyl 2-[(2-sulfan-yl-quinolin-3-yl)methyl-idene]malonate.

In the title compound, C17H17N O4S, the quinoline ring system is nearly planar, with a maximum deviation of 0.0496 (16) Å. A weak intra-molecular C-H⋯O inter-action is observed. In the crystal, C-H⋯O, S-H⋯N and π-π stacking inter-actions between the fused benzene ring of quinoline and the pyridine moieties [shortest centroid-centroid distance = 3.6754 (11) Å] are observed. Inversion-related weak C-H⋯O inter-molecular inter-actions diagonally along [010], with R 2 (2)(10) ring motifs, and S-H⋯N inter-molecular inter-actions diagonally along [100], with R 2 (2)(8) ring motifs, are present, forming a three-dimensional network structure. No classical hydrogen bonds are observed.

Related literature

For biological applications of quinolines, see: Nandeshwarappa et al.(2006 ▸); Noda et al. (2001 ▸); Pandey et al. (2004 ▸); Sharma et al. (2008 ▸).

Experimental

Crystal data

C17H17NO4S

M = 331.37

Triclinic,

a = 7.3739 (4) Å

b = 7.8148 (4) Å

c = 15.8149 (7) Å

α = 90.158 (2)°

β = 99.486 (2)°

γ = 113.301 (2)°

V = 823.24 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▸) T min = 0.770, T max = 1.000

21213 measured reflections

5853 independent reflections

4295 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.213

S = 1.04

5853 reflections

234 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.98 e Å−3

Δρmin = −0.48 e Å−3

Data collection: SMART (Bruker, 2001 ▸); cell refinement: SAINT (Bruker, 2001 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL2014.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015013596/jj2194sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015013596/jj2194Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015013596/jj2194Isup3.cml

Click here for additional data file.

17 17 4 . DOI: 10.1107/S2056989015013596/jj2194fig1.tif

ORTEP diagram of the title compound, C17H17N O4S. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.

Click here for additional data file.

17 17 4 a . DOI: 10.1107/S2056989015013596/jj2194fig2.tif

A view of the packing in the title mol­ecule, C17H17N O4S, along the a axis. Dashed lines indicate weak C—H⋯O and S—H⋯N inter­molecular inter­actions with inversio- related C—H⋯O inter­molecular inter­actions diagonally along [010] with (10) ring motifs and S—H⋯N inter­molecular inter­actions diagonally along [100] with (8) ring motifs forming a three-dimensional network structure.

CCDC reference: 1413116

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

C17H17NO4S	F(000) = 348
Mr = 331.37	Dx = 1.337 Mg m−3
Triclinic, P1	Melting point: 458 K
a = 7.3739 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8148 (4) Å	Cell parameters from 5853 reflections
c = 15.8149 (7) Å	θ = 2.6–32.5°
α = 90.158 (2)°	µ = 0.22 mm−1
β = 99.486 (2)°	T = 296 K
γ = 113.301 (2)°	Plate, yellow
V = 823.24 (7) Å3	0.24 × 0.20 × 0.12 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	5853 independent reflections
Radiation source: fine-focus sealed tube	4295 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 10.0 pixels mm-1	θmax = 32.5°, θmin = 2.6°
ω and φ scans	h = −11→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −11→11
Tmin = 0.770, Tmax = 1.000	l = −23→23
21213 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.213	w = 1/[σ2(Fo2) + (0.1265P)2 + 0.1563P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
5853 reflections	Δρmax = 0.98 e Å−3
234 parameters	Δρmin = −0.48 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.

	x	y	z	Uiso*/Ueq
S1	0.89170 (8)	0.93555 (6)	0.36268 (3)	0.05361 (17)
H1	0.9130	1.0542	0.4163	0.080*
O2	0.9018 (3)	0.6179 (2)	0.10198 (11)	0.0741 (5)
O3	0.6426 (2)	0.3469 (2)	0.05791 (8)	0.0546 (3)
O4	0.5360 (3)	0.1266 (2)	0.23539 (12)	0.0772 (5)
O5	0.3614 (2)	0.2881 (2)	0.17989 (10)	0.0584 (4)
N6	0.8126 (2)	0.71751 (18)	0.48999 (9)	0.0417 (3)
C7	0.8326 (2)	0.7292 (2)	0.40651 (10)	0.0380 (3)
C8	0.7963 (2)	0.5561 (2)	0.35911 (10)	0.0370 (3)
C9	0.7551 (2)	0.3953 (2)	0.40069 (10)	0.0398 (3)
C10	0.7342 (2)	0.3901 (2)	0.48846 (10)	0.0383 (3)
C11	0.7609 (2)	0.5567 (2)	0.53269 (10)	0.0388 (3)
C12	0.7363 (3)	0.5596 (3)	0.61848 (11)	0.0491 (4)
C13	0.6855 (3)	0.3962 (3)	0.65909 (13)	0.0552 (4)
C14	0.6621 (3)	0.2299 (3)	0.61664 (14)	0.0555 (5)
C15	0.6872 (3)	0.2268 (2)	0.53337 (13)	0.0480 (4)
C16	0.8203 (2)	0.5658 (2)	0.26908 (10)	0.0409 (3)
C17	0.7083 (2)	0.4422 (2)	0.20334 (10)	0.0408 (3)
C18	0.5287 (3)	0.2679 (2)	0.20902 (10)	0.0452 (4)
C19	0.7642 (3)	0.4825 (3)	0.11661 (11)	0.0480 (4)
C20	0.1759 (3)	0.1201 (4)	0.17362 (19)	0.0786 (7)
H20A	0.1767	0.0250	0.1343	0.094*
H20B	0.1638	0.0706	0.2296	0.094*
C21	0.0112 (5)	0.1699 (7)	0.1429 (4)	0.153 (2)
H21A	0.0306	0.2843	0.1731	0.229*
H21B	−0.1114	0.0724	0.1525	0.229*
H21C	0.0038	0.1864	0.0825	0.229*
C22	0.6792 (4)	0.3723 (4)	−0.03002 (13)	0.0671 (6)
H22A	0.6744	0.4891	−0.0482	0.081*
H22B	0.8109	0.3761	−0.0333	0.081*
C23	0.5247 (5)	0.2163 (5)	−0.08543 (16)	0.0886 (9)
H23A	0.5372	0.1023	−0.0698	0.133*
H23B	0.5403	0.2350	−0.1442	0.133*
H23C	0.3946	0.2086	−0.0788	0.133*
H9	0.737 (4)	0.276 (4)	0.3721 (18)	0.066 (7)*
H12	0.762 (4)	0.689 (4)	0.6437 (17)	0.063 (7)*
H13	0.658 (4)	0.395 (4)	0.715 (2)	0.079 (8)*
H14	0.628 (5)	0.139 (5)	0.643 (2)	0.081 (9)*
H15	0.659 (4)	0.107 (4)	0.5002 (17)	0.067 (7)*
H16	0.917 (3)	0.662 (3)	0.2553 (14)	0.044 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.0738 (3)	0.0359 (2)	0.0479 (3)	0.0171 (2)	0.0148 (2)	0.00743 (17)
O2	0.0679 (9)	0.0726 (10)	0.0589 (8)	−0.0024 (8)	0.0283 (7)	−0.0006 (7)
O3	0.0549 (7)	0.0603 (8)	0.0379 (6)	0.0098 (6)	0.0140 (5)	−0.0042 (5)
O4	0.0872 (12)	0.0437 (7)	0.0777 (11)	0.0108 (7)	−0.0076 (9)	0.0067 (7)
O5	0.0415 (6)	0.0578 (8)	0.0658 (8)	0.0070 (5)	0.0153 (6)	0.0071 (6)
N6	0.0510 (7)	0.0334 (6)	0.0386 (6)	0.0135 (5)	0.0112 (5)	0.0010 (5)
C7	0.0385 (7)	0.0340 (6)	0.0382 (7)	0.0113 (5)	0.0064 (5)	0.0000 (5)
C8	0.0334 (6)	0.0358 (6)	0.0370 (6)	0.0097 (5)	0.0042 (5)	−0.0023 (5)
C9	0.0377 (7)	0.0339 (6)	0.0426 (7)	0.0109 (5)	0.0021 (5)	−0.0043 (5)
C10	0.0329 (6)	0.0341 (6)	0.0424 (7)	0.0089 (5)	0.0037 (5)	0.0026 (5)
C11	0.0365 (7)	0.0365 (7)	0.0400 (7)	0.0107 (5)	0.0080 (5)	0.0040 (5)
C12	0.0539 (9)	0.0499 (9)	0.0425 (8)	0.0176 (7)	0.0146 (7)	0.0047 (7)
C13	0.0530 (10)	0.0634 (11)	0.0481 (9)	0.0188 (8)	0.0174 (8)	0.0153 (8)
C14	0.0499 (9)	0.0497 (10)	0.0597 (11)	0.0121 (7)	0.0108 (8)	0.0200 (8)
C15	0.0440 (8)	0.0370 (7)	0.0558 (9)	0.0104 (6)	0.0049 (7)	0.0077 (7)
C16	0.0379 (7)	0.0400 (7)	0.0408 (7)	0.0112 (6)	0.0082 (6)	−0.0002 (6)
C17	0.0396 (7)	0.0429 (7)	0.0370 (7)	0.0128 (6)	0.0090 (5)	0.0005 (6)
C18	0.0496 (8)	0.0419 (8)	0.0340 (7)	0.0084 (6)	0.0062 (6)	−0.0028 (6)
C19	0.0449 (8)	0.0536 (9)	0.0419 (8)	0.0142 (7)	0.0128 (6)	0.0002 (7)
C20	0.0509 (11)	0.0720 (15)	0.0844 (16)	−0.0077 (10)	0.0189 (11)	0.0015 (12)
C21	0.0525 (17)	0.125 (3)	0.240 (6)	0.0057 (18)	−0.007 (2)	0.052 (4)
C22	0.0709 (13)	0.0810 (15)	0.0411 (9)	0.0172 (11)	0.0226 (9)	0.0020 (9)
C23	0.115 (2)	0.0886 (19)	0.0448 (11)	0.0240 (17)	0.0127 (12)	−0.0065 (11)

S1—C7	1.6796 (16)	C13—H13	0.94 (3)
S1—H1	1.2000	C14—C15	1.361 (3)
O2—C19	1.197 (2)	C14—H14	0.80 (3)
O3—C19	1.326 (2)	C15—H15	1.00 (3)
O3—C22	1.459 (2)	C16—C17	1.333 (2)
O4—C18	1.199 (2)	C16—H16	0.86 (2)
O5—C18	1.314 (2)	C17—C18	1.494 (2)
O5—C20	1.462 (3)	C17—C19	1.495 (2)
N6—C7	1.352 (2)	C20—C21	1.429 (5)
N6—C11	1.375 (2)	C20—H20A	0.9700
C7—C8	1.451 (2)	C20—H20B	0.9700
C8—C9	1.369 (2)	C21—H21A	0.9600
C8—C16	1.462 (2)	C21—H21B	0.9600
C9—C10	1.421 (2)	C21—H21C	0.9600
C9—H9	0.99 (3)	C22—C23	1.456 (4)
C10—C11	1.403 (2)	C22—H22A	0.9700
C10—C15	1.411 (2)	C22—H22B	0.9700
C11—C12	1.399 (2)	C23—H23A	0.9600
C12—C13	1.374 (3)	C23—H23B	0.9600
C12—H12	1.02 (3)	C23—H23C	0.9600
C13—C14	1.396 (3)
C7—S1—H1	109.5	C16—C17—C18	125.18 (14)
C19—O3—C22	116.21 (16)	C16—C17—C19	117.59 (15)
C18—O5—C20	116.10 (19)	C18—C17—C19	117.22 (14)
C7—N6—C11	125.49 (13)	O4—C18—O5	124.31 (18)
N6—C7—C8	116.36 (14)	O4—C18—C17	124.41 (18)
N6—C7—S1	119.98 (11)	O5—C18—C17	111.27 (15)
C8—C7—S1	123.65 (12)	O2—C19—O3	124.24 (16)
C9—C8—C7	119.72 (14)	O2—C19—C17	124.71 (17)
C9—C8—C16	122.79 (14)	O3—C19—C17	111.04 (15)
C7—C8—C16	117.33 (14)	C21—C20—O5	108.0 (3)
C8—C9—C10	121.62 (14)	C21—C20—H20A	110.1
C8—C9—H9	122.7 (16)	O5—C20—H20A	110.1
C10—C9—H9	115.7 (16)	C21—C20—H20B	110.1
C11—C10—C15	118.31 (15)	O5—C20—H20B	110.1
C11—C10—C9	118.09 (14)	H20A—C20—H20B	108.4
C15—C10—C9	123.61 (15)	C20—C21—H21A	109.5
N6—C11—C12	120.63 (14)	C20—C21—H21B	109.5
N6—C11—C10	118.56 (14)	H21A—C21—H21B	109.5
C12—C11—C10	120.81 (15)	C20—C21—H21C	109.5
C13—C12—C11	118.92 (17)	H21A—C21—H21C	109.5
C13—C12—H12	127.7 (14)	H21B—C21—H21C	109.5
C11—C12—H12	113.3 (14)	C23—C22—O3	108.17 (19)
C12—C13—C14	121.07 (18)	C23—C22—H22A	110.1
C12—C13—H13	119.0 (18)	O3—C22—H22A	110.1
C14—C13—H13	119.8 (18)	C23—C22—H22B	110.1
C15—C14—C13	120.20 (17)	O3—C22—H22B	110.1
C15—C14—H14	124 (2)	H22A—C22—H22B	108.4
C13—C14—H14	116 (2)	C22—C23—H23A	109.5
C14—C15—C10	120.66 (17)	C22—C23—H23B	109.5
C14—C15—H15	121.4 (15)	H23A—C23—H23B	109.5
C10—C15—H15	117.6 (15)	C22—C23—H23C	109.5
C17—C16—C8	127.50 (15)	H23A—C23—H23C	109.5
C17—C16—H16	114.3 (14)	H23B—C23—H23C	109.5
C8—C16—H16	118.2 (14)
C11—N6—C7—C8	−0.1 (2)	C11—C10—C15—C14	2.2 (2)
C11—N6—C7—S1	178.63 (13)	C9—C10—C15—C14	−177.58 (16)
N6—C7—C8—C9	−3.4 (2)	C9—C8—C16—C17	42.8 (3)
S1—C7—C8—C9	177.93 (12)	C7—C8—C16—C17	−141.69 (17)
N6—C7—C8—C16	−179.02 (14)	C8—C16—C17—C18	1.8 (3)
S1—C7—C8—C16	2.3 (2)	C8—C16—C17—C19	−179.45 (16)
C7—C8—C9—C10	4.1 (2)	C20—O5—C18—O4	−5.2 (3)
C16—C8—C9—C10	179.47 (14)	C20—O5—C18—C17	173.63 (17)
C8—C9—C10—C11	−1.3 (2)	C16—C17—C18—O4	−78.9 (3)
C8—C9—C10—C15	178.46 (15)	C19—C17—C18—O4	102.4 (2)
C7—N6—C11—C12	−177.33 (16)	C16—C17—C18—O5	102.3 (2)
C7—N6—C11—C10	2.9 (2)	C19—C17—C18—O5	−76.47 (19)
C15—C10—C11—N6	178.10 (14)	C22—O3—C19—O2	−2.2 (3)
C9—C10—C11—N6	−2.1 (2)	C22—O3—C19—C17	178.64 (18)
C15—C10—C11—C12	−1.7 (2)	C16—C17—C19—O2	−0.2 (3)
C9—C10—C11—C12	178.05 (15)	C18—C17—C19—O2	178.7 (2)
N6—C11—C12—C13	−179.72 (17)	C16—C17—C19—O3	178.96 (16)
C10—C11—C12—C13	0.1 (3)	C18—C17—C19—O3	−2.2 (2)
C11—C12—C13—C14	1.2 (3)	C18—O5—C20—C21	178.7 (3)
C12—C13—C14—C15	−0.7 (3)	C19—O3—C22—C23	−176.6 (2)
C13—C14—C15—C10	−1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
S1—H1···N6i	1.20	2.37	3.3389 (14)	136
C9—H9···O4	0.99 (3)	2.41 (3)	3.122 (2)	129 (2)
C22—H22B···O2ii	0.97	2.52	3.438 (4)	158

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
S1H1N6i	1.20	2.37	3.3389(14)	136
C9H9O4	0.99(3)	2.41(3)	3.122(2)	129(2)
C22H22BO2ii	0.97	2.52	3.438(4)	158

Symmetry codes: (i) ; (ii) .