Crystal structure of (Z)-3-allyl-5-(3-bromo-benzyl-idene)-2-sulfanyl-idene-1,3-thia-zolidin-4-one.

In the title compound, C13H10BrNOS2, the rhodanine (systematic name: 2-sulfanyl-idene-1,3-thia-zolidin-4-one) and the 3-bromo-benzyl-idene ring systems are inclined slightly, forming a dihedral angle of 5.86 (12)°. The rhodanine moiety is linked to an allyl group at the N atom and to the 3-bromo-benzyl-idene ring system. The allyl group, C=C-C, is nearly perpendicular to the mean plane through the rhodanine ring, maling a dihedral angle of 87.2 (5)°. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(10) ring motif.

Related literature

For pharmacological and biological activities of rhodanine-based mol­ecules, see: Tomasić & Masic (2009 ▸); Sortino et al. (2007 ▸); Kesel (2003 ▸); Capan et al. (1996 ▸); Momose et al. (1991 ▸); Kawakami et al. (1998 ▸); Insuasty et al. (2010 ▸). For the crystal structure of a related compound, see: El Ajlaoui et al. (2015 ▸).

Experimental

Crystal data

C13H10BrNOS2

M = 340.25

Triclinic,

a = 5.4044 (6) Å

b = 11.2306 (13) Å

c = 11.7966 (13) Å

α = 80.100 (5)°

β = 84.912 (6)°

γ = 76.732 (6)°

V = 685.60 (13) Å3

Z = 2

Mo Kα radiation

μ = 3.29 mm−1

T = 296 K

0.31 × 0.27 × 0.21 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.479, T max = 0.746

25482 measured reflections

4181 independent reflections

2895 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.098

S = 1.01

4181 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.95 e Å−3

Δρmin = −0.71 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▸), ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015022884/su5249sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015022884/su5249Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015022884/su5249Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015022884/su5249fig1.tif

A view of the mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015022884/su5249fig2.tif

A view along the a axis of the crystal packing of the title compound, showing the hydrogen bonds as dashed lines (see Table 1).

CCDC reference: 1439611

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

C13H10BrNOS2	F(000) = 340
Mr = 340.25	Dx = 1.648 Mg m−3
Triclinic, P1	Melting point: 390 K
a = 5.4044 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2306 (13) Å	Cell parameters from 4181 reflections
c = 11.7966 (13) Å	θ = 2.8–30.5°
α = 80.100 (5)°	µ = 3.29 mm−1
β = 84.912 (6)°	T = 296 K
γ = 76.732 (6)°	Block, colourless
V = 685.60 (13) Å3	0.31 × 0.27 × 0.21 mm
Z = 2

Bruker X8 APEX diffractometer	4181 independent reflections
Radiation source: fine-focus sealed tube	2895 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 30.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.479, Tmax = 0.746	k = −16→16
25482 measured reflections	l = −16→16

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0356P)2 + 0.492P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
4181 reflections	Δρmax = 0.95 e Å−3
163 parameters	Δρmin = −0.71 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
C1	0.7585 (5)	0.8474 (2)	0.6704 (2)	0.0449 (5)
C2	0.7277 (6)	0.8621 (3)	0.5535 (2)	0.0578 (7)
H2	0.7974	0.9201	0.5025	0.069*
C3	0.5914 (6)	0.7891 (3)	0.5138 (2)	0.0625 (8)
H3	0.5704	0.7977	0.4352	0.075*
C4	0.4861 (5)	0.7039 (3)	0.5885 (2)	0.0516 (6)
H4	0.3934	0.6562	0.5601	0.062*
C5	0.5173 (4)	0.6882 (2)	0.70721 (19)	0.0379 (5)
C6	0.6565 (4)	0.7623 (2)	0.7469 (2)	0.0392 (5)
H6	0.6799	0.7540	0.8253	0.047*
C7	0.4177 (4)	0.5987 (2)	0.79133 (19)	0.0386 (5)
H7	0.4638	0.5940	0.8663	0.046*
C8	0.2693 (4)	0.5212 (2)	0.77866 (18)	0.0358 (4)
C9	0.1983 (4)	0.4349 (2)	0.87829 (19)	0.0402 (5)
C10	−0.0140 (4)	0.3884 (2)	0.7315 (2)	0.0385 (5)
C11	−0.0559 (5)	0.2749 (3)	0.9303 (2)	0.0538 (7)
H11A	−0.2218	0.2691	0.9094	0.065*
H11B	−0.0769	0.3018	1.0051	0.065*
C12	0.1173 (8)	0.1500 (3)	0.9393 (3)	0.0717 (9)
H12	0.0739	0.0898	0.9972	0.086*
C13	0.3193 (8)	0.1155 (3)	0.8769 (3)	0.0845 (11)
H13A	0.3724	0.1716	0.8176	0.101*
H13B	0.4125	0.0343	0.8909	0.101*
N1	0.0372 (4)	0.36716 (18)	0.84606 (16)	0.0398 (4)
O1	0.2673 (4)	0.42021 (19)	0.97577 (14)	0.0579 (5)
S1	0.13666 (12)	0.50102 (6)	0.65523 (5)	0.04169 (14)
S2	−0.18899 (14)	0.31940 (7)	0.67061 (6)	0.05491 (18)
Br1	0.94248 (6)	0.94874 (3)	0.72543 (3)	0.06670 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0478 (14)	0.0440 (13)	0.0461 (13)	−0.0140 (11)	−0.0009 (10)	−0.0110 (10)
C2	0.0697 (18)	0.0600 (17)	0.0465 (14)	−0.0269 (14)	0.0026 (13)	−0.0013 (12)
C3	0.080 (2)	0.079 (2)	0.0341 (13)	−0.0327 (17)	−0.0068 (13)	−0.0022 (13)
C4	0.0625 (16)	0.0627 (16)	0.0376 (12)	−0.0268 (13)	−0.0082 (11)	−0.0086 (11)
C5	0.0402 (12)	0.0407 (12)	0.0345 (11)	−0.0097 (9)	−0.0058 (9)	−0.0077 (9)
C6	0.0424 (12)	0.0420 (12)	0.0356 (11)	−0.0106 (10)	−0.0030 (9)	−0.0105 (9)
C7	0.0418 (12)	0.0450 (12)	0.0319 (10)	−0.0102 (10)	−0.0087 (9)	−0.0097 (9)
C8	0.0381 (11)	0.0397 (11)	0.0315 (10)	−0.0072 (9)	−0.0077 (8)	−0.0093 (9)
C9	0.0434 (12)	0.0455 (12)	0.0359 (11)	−0.0142 (10)	−0.0071 (9)	−0.0091 (9)
C10	0.0346 (11)	0.0436 (12)	0.0403 (12)	−0.0059 (9)	−0.0075 (9)	−0.0152 (9)
C11	0.0588 (16)	0.0713 (18)	0.0417 (13)	−0.0359 (14)	0.0026 (11)	−0.0107 (12)
C12	0.106 (3)	0.0573 (18)	0.0569 (18)	−0.0387 (18)	−0.0014 (18)	0.0050 (14)
C13	0.098 (3)	0.060 (2)	0.082 (3)	−0.0004 (19)	−0.008 (2)	0.0036 (18)
N1	0.0432 (10)	0.0464 (11)	0.0345 (9)	−0.0159 (9)	−0.0060 (8)	−0.0085 (8)
O1	0.0756 (13)	0.0754 (13)	0.0335 (9)	−0.0392 (11)	−0.0177 (8)	0.0004 (8)
S1	0.0471 (3)	0.0495 (3)	0.0328 (3)	−0.0148 (3)	−0.0131 (2)	−0.0066 (2)
S2	0.0547 (4)	0.0703 (4)	0.0517 (4)	−0.0268 (3)	−0.0135 (3)	−0.0194 (3)
Br1	0.0796 (2)	0.0688 (2)	0.0663 (2)	−0.04359 (17)	0.00513 (15)	−0.01814 (15)

C1—C6	1.374 (3)	C8—S1	1.749 (2)
C1—C2	1.381 (4)	C9—O1	1.213 (3)
C1—Br1	1.896 (2)	C9—N1	1.394 (3)
C2—C3	1.380 (4)	C10—N1	1.372 (3)
C2—H2	0.9300	C10—S2	1.631 (2)
C3—C4	1.374 (4)	C10—S1	1.739 (2)
C3—H3	0.9300	C11—N1	1.453 (3)
C4—C5	1.401 (3)	C11—C12	1.489 (5)
C4—H4	0.9300	C11—H11A	0.9700
C5—C6	1.401 (3)	C11—H11B	0.9700
C5—C7	1.447 (3)	C12—C13	1.283 (5)
C6—H6	0.9300	C12—H12	0.9300
C7—C8	1.345 (3)	C13—H13A	0.9300
C7—H7	0.9300	C13—H13B	0.9300
C8—C9	1.472 (3)
C6—C1—C2	121.4 (2)	C9—C8—S1	109.66 (16)
C6—C1—Br1	119.79 (18)	O1—C9—N1	122.5 (2)
C2—C1—Br1	118.8 (2)	O1—C9—C8	127.0 (2)
C3—C2—C1	118.7 (2)	N1—C9—C8	110.44 (18)
C3—C2—H2	120.7	N1—C10—S2	126.32 (19)
C1—C2—H2	120.7	N1—C10—S1	110.91 (16)
C4—C3—C2	121.1 (3)	S2—C10—S1	122.77 (14)
C4—C3—H3	119.5	N1—C11—C12	113.0 (2)
C2—C3—H3	119.5	N1—C11—H11A	109.0
C3—C4—C5	120.6 (2)	C12—C11—H11A	109.0
C3—C4—H4	119.7	N1—C11—H11B	109.0
C5—C4—H4	119.7	C12—C11—H11B	109.0
C6—C5—C4	118.1 (2)	H11A—C11—H11B	107.8
C6—C5—C7	117.89 (19)	C13—C12—C11	127.9 (3)
C4—C5—C7	124.0 (2)	C13—C12—H12	116.1
C1—C6—C5	120.2 (2)	C11—C12—H12	116.1
C1—C6—H6	119.9	C12—C13—H13A	120.0
C5—C6—H6	119.9	C12—C13—H13B	120.0
C8—C7—C5	130.5 (2)	H13A—C13—H13B	120.0
C8—C7—H7	114.8	C10—N1—C9	116.30 (19)
C5—C7—H7	114.8	C10—N1—C11	123.3 (2)
C7—C8—C9	120.37 (19)	C9—N1—C11	120.27 (19)
C7—C8—S1	129.97 (18)	C10—S1—C8	92.61 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.93	2.42	3.310 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.93	2.42	3.310 (3)	159

Symmetry code: (i) .