Crystal structure of ethyl 3-anilino-2-{[bis-(methyl-sulfan-yl)methyl-idene]amino}-3-oxopropano-ate.

The mol-ecular conformation of the title compound, C14H18N2O3S2, is stabilized by intra-molecular N-H⋯N and C-H⋯O hydrogen bonds. The crystal packing is characterized by a series of C-H⋯O hydrogen bonds, resulting in a three-dimensional network.

Related literature

For the synthesis and cytotoxic activity of thia­zolo[5,4-b]quinoline derivatives, see: Rodríguez-Loaiza et al. (2004 ▶); Loza-Mejía et al. (2008 ▶, 2009 ▶); Adams et al. (2002 ▶).

Experimental

Crystal data

C14H18N2O3S2

M = 326.42

Triclinic,

a = 8.5298 (11) Å

b = 9.1422 (16) Å

c = 11.0268 (13) Å

α = 101.377 (12)°

β = 102.102 (10)°

γ = 104.457 (13)°

V = 785.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 145 K

0.6 × 0.5 × 0.35 mm

Data collection

Agilent Xcalibur Atlas Gemini diffractometer

Absorption correction: analytical (CrysAlis RED; Agilent, 2012 ▶) T min = 0.87, T max = 0.922

5879 measured reflections

3625 independent reflections

3022 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.101

S = 1.05

3625 reflections

197 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814016560/bt6988sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016560/bt6988Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016560/bt6988Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814016560/bt6988fig1.tif

The mol­ecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as circles of arbitrary size.

Click here for additional data file.

. DOI: 10.1107/S1600536814016560/bt6988fig2.tif

Crystal packing with inter­molecular inter­actions of type C—H⋯O forming a three-dimensional network.

CCDC reference: 1014381

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

C14H18N2O3S2	Z = 2
Mr = 326.42	F(000) = 344
Triclinic, P1	Dx = 1.38 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5298 (11) Å	Cell parameters from 2290 reflections
b = 9.1422 (16) Å	θ = 3.6–29.4°
c = 11.0268 (13) Å	µ = 0.35 mm−1
α = 101.377 (12)°	T = 145 K
β = 102.102 (10)°	Block, colourless
γ = 104.457 (13)°	0.6 × 0.5 × 0.35 mm
V = 785.3 (2) Å3

Agilent Xcalibur Atlas Gemini diffractometer	3625 independent reflections
Graphite monochromator	3022 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.028
ω scans	θmax = 29.4°, θmin = 3.6°
Absorption correction: analytical (CrysAlis RED; Agilent, 2012)	h = −11→11
Tmin = 0.87, Tmax = 0.922	k = −9→11
5879 measured reflections	l = −15→14

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0448P)2 + 0.1551P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.039	(Δ/σ)max < 0.001
wR(F2) = 0.101	Δρmax = 0.34 e Å−3
S = 1.05	Δρmin = −0.36 e Å−3
3625 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
197 parameters	Extinction coefficient: 0.033 (3)
1 restraint

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
C1	0.22485 (19)	0.68715 (19)	0.59186 (14)	0.0184 (3)
C2	0.1478 (2)	0.8032 (2)	0.57936 (16)	0.0216 (4)
H2	0.0786	0.7997	0.4985	0.026*
C3	0.1738 (2)	0.9243 (2)	0.68710 (16)	0.0260 (4)
H3	0.1217	1.0038	0.6792	0.031*
C4	0.2741 (2)	0.9311 (2)	0.80562 (17)	0.0289 (4)
H4	0.2909	1.0146	0.8784	0.035*
C5	0.3498 (2)	0.8150 (2)	0.81709 (16)	0.0276 (4)
H5	0.4188	0.819	0.8981	0.033*
C6	0.3254 (2)	0.6930 (2)	0.71085 (16)	0.0241 (4)
H6	0.3773	0.6135	0.7193	0.029*
C7	0.13582 (19)	0.5349 (2)	0.36177 (15)	0.0194 (3)
C8	0.1513 (2)	0.38584 (19)	0.27795 (14)	0.0187 (3)
H8	0.0362	0.3141	0.2294	0.022*
C9	0.24576 (19)	0.43850 (19)	0.18264 (15)	0.0188 (3)
C10	0.2175 (2)	0.4733 (2)	−0.02788 (15)	0.0244 (4)
H10A	0.3176	0.5663	0.0132	0.029*
H10B	0.1363	0.5023	−0.0897	0.029*
C11	0.2686 (2)	0.3427 (2)	−0.09767 (18)	0.0325 (4)
H11A	0.315	0.3746	−0.1659	0.049*
H11B	0.1701	0.2496	−0.1356	0.049*
H11C	0.3541	0.3186	−0.0372	0.049*
C12	0.2467 (2)	0.1698 (2)	0.31142 (14)	0.0195 (3)
C13	0.2088 (2)	−0.1139 (2)	0.13307 (17)	0.0294 (4)
H13A	0.1576	−0.18	0.0448	0.044*
H13B	0.1628	−0.1673	0.1925	0.044*
H13C	0.3309	−0.0944	0.1545	0.044*
C14	0.4017 (3)	0.2120 (2)	0.56368 (16)	0.0317 (4)
H14A	0.4778	0.3092	0.5589	0.048*
H14B	0.4595	0.1723	0.6305	0.048*
H14C	0.3018	0.2324	0.5847	0.048*
N1	0.20693 (17)	0.56002 (17)	0.48823 (12)	0.0200 (3)
N2	0.23886 (17)	0.30580 (16)	0.35854 (12)	0.0200 (3)
O1	0.06584 (17)	0.61847 (16)	0.31231 (11)	0.0308 (3)
O2	0.39713 (14)	0.48975 (15)	0.20888 (11)	0.0265 (3)
O3	0.14030 (13)	0.42455 (14)	0.07059 (10)	0.0217 (3)
S1	0.16283 (5)	0.06980 (5)	0.14655 (4)	0.02388 (13)
S2	0.33924 (6)	0.06874 (5)	0.41135 (4)	0.02561 (14)
H1F	0.254 (2)	0.487 (2)	0.5037 (18)	0.031*

	U11	U22	U33	U12	U13	U23
C1	0.0190 (7)	0.0190 (9)	0.0168 (7)	0.0042 (6)	0.0079 (6)	0.0029 (6)
C2	0.0246 (8)	0.0205 (9)	0.0218 (8)	0.0075 (7)	0.0089 (7)	0.0064 (7)
C3	0.0335 (9)	0.0187 (9)	0.0300 (9)	0.0100 (7)	0.0155 (8)	0.0061 (7)
C4	0.0343 (9)	0.0227 (10)	0.0251 (9)	0.0037 (8)	0.0121 (8)	−0.0017 (7)
C5	0.0272 (9)	0.0317 (11)	0.0187 (8)	0.0059 (8)	0.0030 (7)	0.0024 (7)
C6	0.0243 (8)	0.0268 (10)	0.0220 (8)	0.0095 (7)	0.0061 (7)	0.0059 (7)
C7	0.0205 (7)	0.0190 (9)	0.0189 (7)	0.0062 (6)	0.0062 (7)	0.0044 (6)
C8	0.0210 (7)	0.0178 (8)	0.0165 (7)	0.0065 (6)	0.0035 (6)	0.0040 (6)
C9	0.0217 (8)	0.0162 (8)	0.0182 (7)	0.0080 (6)	0.0036 (7)	0.0025 (6)
C10	0.0272 (8)	0.0315 (10)	0.0191 (8)	0.0124 (7)	0.0075 (7)	0.0113 (7)
C11	0.0356 (10)	0.0377 (12)	0.0288 (9)	0.0133 (9)	0.0161 (8)	0.0086 (8)
C12	0.0212 (7)	0.0201 (9)	0.0177 (7)	0.0057 (6)	0.0062 (7)	0.0055 (6)
C13	0.0382 (10)	0.0196 (9)	0.0280 (9)	0.0107 (8)	0.0077 (8)	−0.0001 (7)
C14	0.0426 (10)	0.0306 (11)	0.0177 (8)	0.0121 (9)	−0.0001 (8)	0.0043 (7)
N1	0.0251 (7)	0.0197 (8)	0.0175 (6)	0.0116 (6)	0.0057 (6)	0.0040 (5)
N2	0.0243 (7)	0.0189 (7)	0.0173 (6)	0.0082 (6)	0.0048 (6)	0.0049 (5)
O1	0.0461 (7)	0.0291 (7)	0.0208 (6)	0.0229 (6)	0.0034 (6)	0.0061 (5)
O2	0.0202 (6)	0.0324 (8)	0.0245 (6)	0.0052 (5)	0.0029 (5)	0.0092 (5)
O3	0.0208 (6)	0.0300 (7)	0.0153 (5)	0.0094 (5)	0.0038 (5)	0.0072 (5)
S1	0.0304 (2)	0.0213 (2)	0.0173 (2)	0.00912 (18)	0.00318 (17)	0.00107 (16)
S2	0.0351 (3)	0.0212 (2)	0.0211 (2)	0.01201 (19)	0.00365 (19)	0.00657 (17)

C1—C6	1.392 (2)	C10—O3	1.4683 (19)
C1—C2	1.395 (2)	C10—C11	1.498 (3)
C1—N1	1.412 (2)	C10—H10A	0.99
C2—C3	1.390 (2)	C10—H10B	0.99
C2—H2	0.95	C11—H11A	0.98
C3—C4	1.384 (3)	C11—H11B	0.98
C3—H3	0.95	C11—H11C	0.98
C4—C5	1.386 (3)	C12—N2	1.273 (2)
C4—H4	0.95	C12—S2	1.7587 (17)
C5—C6	1.388 (2)	C12—S1	1.7678 (16)
C5—H5	0.95	C13—S1	1.8035 (19)
C6—H6	0.95	C13—H13A	0.98
C7—O1	1.2217 (19)	C13—H13B	0.98
C7—N1	1.347 (2)	C13—H13C	0.98
C7—C8	1.541 (2)	C14—S2	1.7968 (18)
C8—N2	1.461 (2)	C14—H14A	0.98
C8—C9	1.532 (2)	C14—H14B	0.98
C8—H8	1	C14—H14C	0.98
C9—O2	1.2075 (19)	N1—H1F	0.889 (15)
C9—O3	1.3292 (18)
C6—C1—C2	120.11 (15)	C11—C10—H10A	109.6
C6—C1—N1	116.63 (15)	O3—C10—H10B	109.6
C2—C1—N1	123.25 (14)	C11—C10—H10B	109.6
C3—C2—C1	118.97 (16)	H10A—C10—H10B	108.2
C3—C2—H2	120.5	C10—C11—H11A	109.5
C1—C2—H2	120.5	C10—C11—H11B	109.5
C4—C3—C2	121.22 (17)	H11A—C11—H11B	109.5
C4—C3—H3	119.4	C10—C11—H11C	109.5
C2—C3—H3	119.4	H11A—C11—H11C	109.5
C3—C4—C5	119.36 (16)	H11B—C11—H11C	109.5
C3—C4—H4	120.3	N2—C12—S2	120.47 (12)
C5—C4—H4	120.3	N2—C12—S1	123.28 (12)
C4—C5—C6	120.39 (16)	S2—C12—S1	116.23 (10)
C4—C5—H5	119.8	S1—C13—H13A	109.5
C6—C5—H5	119.8	S1—C13—H13B	109.5
C5—C6—C1	119.94 (17)	H13A—C13—H13B	109.5
C5—C6—H6	120	S1—C13—H13C	109.5
C1—C6—H6	120	H13A—C13—H13C	109.5
O1—C7—N1	126.13 (16)	H13B—C13—H13C	109.5
O1—C7—C8	120.39 (14)	S2—C14—H14A	109.5
N1—C7—C8	113.48 (14)	S2—C14—H14B	109.5
N2—C8—C9	112.30 (13)	H14A—C14—H14B	109.5
N2—C8—C7	110.24 (12)	S2—C14—H14C	109.5
C9—C8—C7	106.50 (13)	H14A—C14—H14C	109.5
N2—C8—H8	109.2	H14B—C14—H14C	109.5
C9—C8—H8	109.2	C7—N1—C1	129.37 (14)
C7—C8—H8	109.2	C7—N1—H1F	111.8 (13)
O2—C9—O3	125.06 (15)	C1—N1—H1F	118.7 (13)
O2—C9—C8	123.37 (14)	C12—N2—C8	120.84 (13)
O3—C9—C8	111.54 (13)	C9—O3—C10	116.15 (12)
O3—C10—C11	110.09 (15)	C12—S1—C13	104.78 (8)
O3—C10—H10A	109.6	C12—S2—C14	99.96 (8)
C6—C1—C2—C3	0.3 (2)	O1—C7—N1—C1	−2.9 (3)
N1—C1—C2—C3	−179.69 (15)	C8—C7—N1—C1	176.35 (15)
C1—C2—C3—C4	−0.1 (3)	C6—C1—N1—C7	−171.05 (16)
C2—C3—C4—C5	−0.1 (3)	C2—C1—N1—C7	8.9 (3)
C3—C4—C5—C6	0.0 (3)	S2—C12—N2—C8	−175.45 (11)
C4—C5—C6—C1	0.2 (3)	S1—C12—N2—C8	2.8 (2)
C2—C1—C6—C5	−0.4 (2)	C9—C8—N2—C12	−70.50 (19)
N1—C1—C6—C5	179.60 (15)	C7—C8—N2—C12	170.92 (14)
O1—C7—C8—N2	−179.82 (15)	O2—C9—O3—C10	1.2 (2)
N1—C7—C8—N2	0.92 (19)	C8—C9—O3—C10	179.46 (13)
O1—C7—C8—C9	58.11 (19)	C11—C10—O3—C9	83.60 (18)
N1—C7—C8—C9	−121.15 (14)	N2—C12—S1—C13	179.81 (14)
N2—C8—C9—O2	−38.3 (2)	S2—C12—S1—C13	−1.86 (12)
C7—C8—C9—O2	82.41 (19)	N2—C12—S2—C14	−1.14 (16)
N2—C8—C9—O3	143.40 (13)	S1—C12—S2—C14	−179.52 (10)
C7—C8—C9—O3	−95.84 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1F···N2	0.889 (15)	2.019 (18)	2.586 (2)	120.5 (15)
C2—H2···O1	0.95	2.33	2.932 (2)	121
C6—H6···O2i	0.95	2.4	3.295 (2)	156
C10—H10B···O1ii	0.99	2.53	3.340 (2)	138
C10—H10B···O3ii	0.99	2.65	3.377 (2)	131
C11—H11A···O2iii	0.98	2.64	3.465 (2)	141
C13—H13B···O1iv	0.98	2.63	3.579 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1F⋯N2	0.889 (15)	2.019 (18)	2.586 (2)	120.5 (15)
C2—H2⋯O1	0.95	2.33	2.932 (2)	121
C6—H6⋯O2i	0.95	2.4	3.295 (2)	156
C10—H10B⋯O1ii	0.99	2.53	3.340 (2)	138
C10—H10B⋯O3ii	0.99	2.65	3.377 (2)	131
C11—H11A⋯O2iii	0.98	2.64	3.465 (2)	141
C13—H13B⋯O1iv	0.98	2.63	3.579 (2)	162

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .