3,3-Bis(methyl-sulfan-yl)-1-(4-nitro-phen-yl)prop-2-en-1-one.

In the title compound, C11H11NO3S2, the S-Csp (2) bonds are shorter [1.746 (3) and 1.750 (2) Å] than the S-CH3 bonds [1.794 (3) and 1.806 (3) Å], which we attribute to d-π inter-actions between the S atoms and the C=C bond. The 1,1-bis-(methyl-sulfan-yl)-3-oxo-propyl-ene fragment and the 4-nitro-phenyl group are both almost planar, with the largest deviations from their mean planes being 0.053 (1) and 0.017 (2) Å, respectively. The dihedral angle between the two planes is 35.07 (7)°. Mol-ecules in the crystal are linked into a three-dimensional network by C-H⋯S and C-H⋯O hydrogen bonds.

Related literature

For the synthesis of the title compound, see: Huang & Liu (1989 ▶). For applications, see: Barun et al. (2000 ▶); Kuettel et al. (2007 ▶). For general background on ketene aminals, see: Huang & Wang (1994 ▶).

Experimental

Crystal data

C11H11NO3S2

M = 269.33

Triclinic,

a = 7.917 (2) Å

b = 8.739 (2) Å

c = 9.574 (3) Å

α = 70.415 (13)°

β = 81.985 (14)°

γ = 73.283 (13)°

V = 597.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.44 mm−1

T = 173 K

0.27 × 0.24 × 0.05 mm

Data collection

Rigaku Saturn724+ CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.581, T max = 1.000

7843 measured reflections

2719 independent reflections

2394 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.115

S = 1.15

2719 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014542/fy2092sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014542/fy2092Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014542/fy2092Isup3.cml

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

Enhanced figure: interactive version of Fig. 1

C11H11NO3S2	Z = 2
Mr = 269.33	F(000) = 280
Triclinic, P1	Dx = 1.498 Mg m−3
a = 7.917 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.739 (2) Å	Cell parameters from 2392 reflections
c = 9.574 (3) Å	θ = 2.3–32.6°
α = 70.415 (13)°	µ = 0.44 mm−1
β = 81.985 (14)°	T = 173 K
γ = 73.283 (13)°	Plate, yellow
V = 597.0 (3) Å3	0.27 × 0.24 × 0.05 mm

Saturn724+ CCD diffractometer	2719 independent reflections
Radiation source: sealed tube	2394 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
ω scans at fixed χ = 45°	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	h = −10→10
Tmin = 0.581, Tmax = 1.000	k = −11→11
7843 measured reflections	l = −12→12

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0306P)2 + 0.3933P] where P = (Fo2 + 2Fc2)/3
2719 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.23 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
S1	1.24009 (8)	0.08728 (8)	0.14324 (8)	0.03498 (19)
S2	1.38394 (8)	0.37041 (8)	0.12260 (7)	0.03303 (18)
O1	1.1193 (2)	0.6171 (2)	0.1933 (2)	0.0386 (4)
O2	0.2086 (2)	0.7642 (3)	0.4617 (2)	0.0429 (5)
O3	0.3377 (3)	0.8672 (3)	0.5789 (2)	0.0518 (6)
N1	0.3402 (3)	0.7914 (3)	0.4916 (2)	0.0338 (5)
C1	1.0268 (3)	0.0451 (3)	0.1766 (3)	0.0404 (6)
H1A	0.9467	0.1298	0.1022	0.061*
H1B	0.9799	0.0492	0.2759	0.061*
H1C	1.0375	−0.0668	0.1698	0.061*
C2	1.5600 (3)	0.2069 (4)	0.0782 (3)	0.0398 (6)
H2A	1.5239	0.1753	0.0001	0.060*
H2B	1.5857	0.1086	0.1670	0.060*
H2C	1.6660	0.2481	0.0434	0.060*
C3	1.2001 (3)	0.2871 (3)	0.1613 (3)	0.0280 (5)
C4	1.0404 (3)	0.3722 (3)	0.2043 (3)	0.0297 (5)
H4	0.9447	0.3218	0.2225	0.036*
C5	1.0078 (3)	0.5353 (3)	0.2239 (3)	0.0299 (5)
C6	0.8303 (3)	0.6031 (3)	0.2912 (3)	0.0273 (5)
C7	0.8213 (3)	0.6942 (3)	0.3879 (3)	0.0309 (5)
H7	0.9257	0.7142	0.4083	0.037*
C8	0.6607 (3)	0.7558 (3)	0.4548 (3)	0.0321 (5)
H8	0.6540	0.8155	0.5229	0.038*
C9	0.5109 (3)	0.7280 (3)	0.4199 (3)	0.0280 (5)
C10	0.5143 (3)	0.6403 (3)	0.3229 (3)	0.0300 (5)
H10	0.4088	0.6243	0.3002	0.036*
C11	0.6762 (3)	0.5765 (3)	0.2597 (3)	0.0292 (5)
H11	0.6823	0.5139	0.1941	0.035*

	U11	U22	U33	U12	U13	U23
S1	0.0283 (3)	0.0309 (3)	0.0462 (4)	−0.0060 (3)	0.0047 (3)	−0.0165 (3)
S2	0.0256 (3)	0.0382 (4)	0.0383 (4)	−0.0103 (3)	0.0037 (3)	−0.0160 (3)
O1	0.0320 (10)	0.0386 (10)	0.0522 (12)	−0.0155 (8)	0.0104 (8)	−0.0227 (9)
O2	0.0277 (10)	0.0525 (12)	0.0472 (12)	−0.0118 (9)	0.0037 (8)	−0.0150 (10)
O3	0.0423 (12)	0.0650 (14)	0.0573 (13)	−0.0078 (10)	0.0109 (10)	−0.0411 (12)
N1	0.0305 (11)	0.0329 (11)	0.0342 (12)	−0.0064 (9)	0.0031 (9)	−0.0090 (10)
C1	0.0329 (14)	0.0321 (13)	0.0599 (18)	−0.0101 (12)	0.0026 (13)	−0.0194 (13)
C2	0.0242 (13)	0.0458 (16)	0.0479 (16)	−0.0069 (12)	0.0054 (11)	−0.0174 (13)
C3	0.0272 (12)	0.0304 (12)	0.0264 (12)	−0.0082 (10)	−0.0004 (9)	−0.0088 (10)
C4	0.0274 (12)	0.0296 (12)	0.0332 (13)	−0.0093 (10)	0.0022 (10)	−0.0108 (11)
C5	0.0295 (12)	0.0326 (13)	0.0303 (13)	−0.0114 (11)	0.0019 (10)	−0.0118 (10)
C6	0.0293 (12)	0.0252 (11)	0.0271 (12)	−0.0077 (10)	0.0005 (9)	−0.0077 (10)
C7	0.0270 (12)	0.0320 (13)	0.0371 (14)	−0.0109 (10)	0.0023 (10)	−0.0139 (11)
C8	0.0357 (14)	0.0327 (13)	0.0323 (13)	−0.0111 (11)	0.0010 (10)	−0.0150 (11)
C9	0.0271 (12)	0.0268 (12)	0.0265 (12)	−0.0052 (10)	0.0027 (9)	−0.0067 (10)
C10	0.0275 (12)	0.0292 (12)	0.0326 (13)	−0.0086 (10)	−0.0031 (10)	−0.0070 (10)
C11	0.0304 (12)	0.0306 (12)	0.0295 (12)	−0.0073 (10)	−0.0016 (10)	−0.0136 (10)

S1—C3	1.746 (3)	C3—C4	1.357 (3)
S1—C1	1.794 (3)	C4—C5	1.444 (3)
S2—C3	1.750 (2)	C4—H4	0.9500
S2—C2	1.806 (3)	C5—C6	1.505 (3)
O1—C5	1.236 (3)	C6—C7	1.392 (3)
O2—N1	1.223 (3)	C6—C11	1.395 (3)
O3—N1	1.223 (3)	C7—C8	1.389 (3)
N1—C9	1.473 (3)	C7—H7	0.9500
C1—H1A	0.9800	C8—C9	1.381 (3)
C1—H1B	0.9800	C8—H8	0.9500
C1—H1C	0.9800	C9—C10	1.381 (3)
C2—H2A	0.9800	C10—C11	1.385 (3)
C2—H2B	0.9800	C10—H10	0.9500
C2—H2C	0.9800	C11—H11	0.9500
C3—S1—C1	104.01 (12)	C5—C4—H4	118.2
C3—S2—C2	103.83 (12)	O1—C5—C4	123.4 (2)
O2—N1—O3	123.4 (2)	O1—C5—C6	119.3 (2)
O2—N1—C9	118.3 (2)	C4—C5—C6	117.2 (2)
O3—N1—C9	118.3 (2)	C7—C6—C11	119.6 (2)
S1—C1—H1A	109.5	C7—C6—C5	118.6 (2)
S1—C1—H1B	109.5	C11—C6—C5	121.8 (2)
H1A—C1—H1B	109.5	C8—C7—C6	120.4 (2)
S1—C1—H1C	109.5	C8—C7—H7	119.8
H1A—C1—H1C	109.5	C6—C7—H7	119.8
H1B—C1—H1C	109.5	C9—C8—C7	118.3 (2)
S2—C2—H2A	109.5	C9—C8—H8	120.9
S2—C2—H2B	109.5	C7—C8—H8	120.9
H2A—C2—H2B	109.5	C10—C9—C8	123.0 (2)
S2—C2—H2C	109.5	C10—C9—N1	118.4 (2)
H2A—C2—H2C	109.5	C8—C9—N1	118.6 (2)
H2B—C2—H2C	109.5	C9—C10—C11	118.0 (2)
C4—C3—S1	123.37 (19)	C9—C10—H10	121.0
C4—C3—S2	121.71 (19)	C11—C10—H10	121.0
S1—C3—S2	114.92 (14)	C10—C11—C6	120.8 (2)
C3—C4—C5	123.6 (2)	C10—C11—H11	119.6
C3—C4—H4	118.2	C6—C11—H11	119.6
C1—S1—C3—C4	5.0 (3)	C5—C6—C7—C8	−178.6 (2)
C1—S1—C3—S2	−176.01 (14)	C6—C7—C8—C9	−1.6 (4)
C2—S2—C3—C4	178.0 (2)	C7—C8—C9—C10	0.7 (4)
C2—S2—C3—S1	−0.99 (17)	C7—C8—C9—N1	179.4 (2)
S1—C3—C4—C5	178.02 (19)	O2—N1—C9—C10	−0.3 (3)
S2—C3—C4—C5	−0.9 (4)	O3—N1—C9—C10	179.1 (2)
C3—C4—C5—O1	5.3 (4)	O2—N1—C9—C8	−179.0 (2)
C3—C4—C5—C6	−172.2 (2)	O3—N1—C9—C8	0.4 (3)
O1—C5—C6—C7	−34.5 (3)	C8—C9—C10—C11	0.7 (4)
C4—C5—C6—C7	143.0 (2)	N1—C9—C10—C11	−178.0 (2)
O1—C5—C6—C11	145.8 (2)	C9—C10—C11—C6	−1.2 (4)
C4—C5—C6—C11	−36.7 (3)	C7—C6—C11—C10	0.4 (4)
C11—C6—C7—C8	1.1 (4)	C5—C6—C11—C10	−180.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···S2i	0.95	2.93	3.614 (3)	130
C8—H8···O3ii	0.95	2.63	3.204 (3)	119
C2—H2B···O3iii	0.98	2.68	3.297 (4)	122
C10—H10···O1iv	0.95	2.66	3.602 (3)	171
C1—H1C···O1v	0.98	2.59	3.551 (3)	167
C7—H7···O2vi	0.95	2.55	3.499 (3)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯S2i	0.95	2.93	3.614 (3)	130
C8—H8⋯O3ii	0.95	2.63	3.204 (3)	119
C2—H2B⋯O3iii	0.98	2.68	3.297 (4)	122
C10—H10⋯O1iv	0.95	2.66	3.602 (3)	171
C1—H1C⋯O1v	0.98	2.59	3.551 (3)	167
C7—H7⋯O2vi	0.95	2.55	3.499 (3)	179

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