1-Acetyl-5-(4-fluoro-phen-yl)-2-sulfanyl-ideneimidazolidin-4-one.

In the title compound, C11H9FN2O2S, the 2-sulfanylideneimidazolidin-4-one moiety is essentially planar, with a maximum deviation of 0.0183 (14) Å. The mean plane of this moiety is approximately coplanar with the attached acetyl group and perpendicular to the benzene ring, making dihedral angles of 9.70 (14) and 86.70 (6)°, respectively. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds between the amide NH and acetyl C=O groups, forming a C(6) chain along the a-axis direction.

Related literature

For applications and the biological activity of 2-sulfanylideneimidazolidin-4-ones, see: Marton et al. (1993 ▶). For the crystal structures of related compounds, see: Casas et al. (1998 ▶); Sulbaran et al. (2007 ▶); Taniguchi et al. (2009 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For hydrogen-bond motifs, see: Etter (1990 ▶). For the synthetic procedure, see: Schlack & Kumpf (1926 ▶).

Experimental

Crystal data

C11H9FN2O2S

M = 252.27

Monoclinic,

a = 7.1327 (9) Å

b = 23.852 (3) Å

c = 7.3437 (10) Å

β = 113.541 (3)°

V = 1145.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 123 K

0.30 × 0.10 × 0.08 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Rigaku, 1998 ▶) T min = 0.829, T max = 0.977

12234 measured reflections

2612 independent reflections

2418 reflections with F 2 > 2σ(F 2)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.082

S = 1.06

2612 reflections

159 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR2008 in Il Milione (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 2010 ▶).

Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S1600536813028560/is5315sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028560/is5315Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028560/is5315Isup3.cml

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

C11H9FN2O2S	F(000) = 520
Mr = 252.27	Dx = 1.463 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 4829 reflections
a = 7.1327 (9) Å	θ = 3.0–27.5°
b = 23.852 (3) Å	µ = 0.29 mm−1
c = 7.3437 (10) Å	T = 123 K
β = 113.541 (3)°	Prism, colorless
V = 1145.4 (3) Å3	0.30 × 0.10 × 0.08 mm
Z = 4

Rigaku/MSC Mercury CCD diffractometer	2418 reflections with F2 > 2σ(F2)
Detector resolution: 7.314 pixels mm-1	Rint = 0.024
ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	h = −9→9
Tmin = 0.829, Tmax = 0.977	k = −30→30
12234 measured reflections	l = −9→8
2612 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.4044P] where P = (Fo2 + 2Fc2)/3
2612 reflections	(Δ/σ)max = 0.001
159 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods

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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
S1	0.92257 (4)	0.464054 (12)	0.18414 (4)	0.02040 (10)
F1	0.66717 (16)	0.18005 (4)	0.78913 (15)	0.0472 (3)
O1	1.28538 (13)	0.37499 (4)	0.83947 (13)	0.0254 (2)
O2	0.53419 (13)	0.42791 (4)	0.53528 (13)	0.0240 (2)
N1	0.81733 (14)	0.42098 (4)	0.47872 (14)	0.0166 (2)
N2	1.14408 (15)	0.41667 (4)	0.53118 (15)	0.0180 (2)
C1	0.95711 (17)	0.43386 (4)	0.39663 (17)	0.0164 (3)
C2	1.14023 (17)	0.39352 (5)	0.70131 (17)	0.0186 (3)
C3	0.91869 (16)	0.39534 (5)	0.67800 (16)	0.0166 (3)
C4	0.61024 (17)	0.43576 (5)	0.41600 (18)	0.0187 (3)
C5	0.49412 (19)	0.45857 (6)	0.21277 (19)	0.0265 (3)
C6	0.84028 (17)	0.33792 (5)	0.69937 (17)	0.0184 (3)
C7	0.7772 (2)	0.32809 (5)	0.8518 (2)	0.0264 (3)
C8	0.7187 (3)	0.27457 (6)	0.8832 (2)	0.0338 (4)
C9	0.7236 (3)	0.23252 (6)	0.7578 (3)	0.0314 (3)
C10	0.7823 (3)	0.24057 (6)	0.6034 (2)	0.0304 (3)
C11	0.8411 (2)	0.29430 (5)	0.57419 (19)	0.0249 (3)
H2	1.252 (3)	0.4205 (7)	0.513 (3)	0.027 (4)*
H3	0.9063	0.4211	0.7800	0.0199*
H5A	0.3491	0.4617	0.1885	0.0318*
H5B	0.5095	0.4333	0.1143	0.0318*
H5C	0.5474	0.4957	0.2019	0.0318*
H7	0.7738	0.3581	0.9356	0.0317*
H8	0.6765	0.2673	0.9884	0.0406*
H10	0.7828	0.2104	0.5189	0.0364*
H11	0.8822	0.3012	0.4681	0.0299*

	U11	U22	U33	U12	U13	U23
S1	0.02194 (17)	0.02105 (16)	0.02123 (17)	0.00019 (10)	0.01181 (13)	0.00233 (10)
F1	0.0632 (7)	0.0242 (5)	0.0522 (6)	−0.0180 (4)	0.0208 (5)	0.0062 (4)
O1	0.0181 (5)	0.0278 (5)	0.0267 (5)	0.0001 (4)	0.0052 (4)	0.0056 (4)
O2	0.0175 (4)	0.0300 (5)	0.0283 (5)	0.0008 (4)	0.0131 (4)	0.0028 (4)
N1	0.0148 (5)	0.0173 (5)	0.0188 (5)	−0.0003 (4)	0.0078 (4)	0.0014 (4)
N2	0.0141 (5)	0.0196 (5)	0.0223 (5)	−0.0004 (4)	0.0095 (4)	−0.0004 (4)
C1	0.0170 (5)	0.0122 (5)	0.0220 (6)	−0.0019 (4)	0.0099 (5)	−0.0034 (4)
C2	0.0183 (6)	0.0156 (5)	0.0231 (6)	−0.0024 (4)	0.0094 (5)	−0.0016 (4)
C3	0.0162 (6)	0.0163 (6)	0.0179 (6)	−0.0008 (4)	0.0075 (5)	0.0006 (4)
C4	0.0153 (6)	0.0183 (6)	0.0235 (6)	−0.0011 (5)	0.0087 (5)	−0.0018 (5)
C5	0.0174 (6)	0.0386 (8)	0.0229 (6)	0.0029 (5)	0.0072 (5)	0.0036 (5)
C6	0.0151 (5)	0.0180 (6)	0.0218 (6)	−0.0016 (4)	0.0072 (5)	0.0006 (5)
C7	0.0316 (7)	0.0243 (7)	0.0279 (7)	−0.0064 (5)	0.0168 (6)	−0.0020 (5)
C8	0.0424 (8)	0.0321 (8)	0.0323 (7)	−0.0116 (6)	0.0205 (7)	0.0034 (6)
C9	0.0326 (7)	0.0207 (6)	0.0370 (8)	−0.0097 (6)	0.0098 (6)	0.0061 (6)
C10	0.0363 (8)	0.0187 (6)	0.0353 (8)	−0.0058 (6)	0.0135 (6)	−0.0051 (5)
C11	0.0284 (7)	0.0219 (6)	0.0278 (7)	−0.0035 (5)	0.0146 (6)	−0.0022 (5)

S1—C1	1.6454 (13)	C7—C8	1.391 (2)
F1—C9	1.3621 (19)	C8—C9	1.372 (3)
O1—C2	1.2073 (13)	C9—C10	1.370 (3)
O2—C4	1.2150 (19)	C10—C11	1.392 (2)
N1—C1	1.3899 (19)	N2—H2	0.84 (2)
N1—C3	1.4810 (14)	C3—H3	1.000
N1—C4	1.4053 (16)	C5—H5A	0.980
N2—C1	1.3676 (14)	C5—H5B	0.980
N2—C2	1.3762 (18)	C5—H5C	0.980
C2—C3	1.5206 (18)	C7—H7	0.950
C3—C6	1.5111 (18)	C8—H8	0.950
C4—C5	1.4906 (17)	C10—H10	0.950
C6—C7	1.383 (3)	C11—H11	0.950
C6—C11	1.3900 (19)
C1—N1—C3	111.61 (9)	C8—C9—C10	123.48 (15)
C1—N1—C4	130.13 (10)	C9—C10—C11	117.85 (14)
C3—N1—C4	117.51 (11)	C6—C11—C10	120.41 (15)
C1—N2—C2	114.14 (12)	C1—N2—H2	123.1 (10)
S1—C1—N1	130.27 (8)	C2—N2—H2	122.7 (10)
S1—C1—N2	123.36 (11)	N1—C3—H3	109.392
N1—C1—N2	106.37 (11)	C2—C3—H3	109.399
O1—C2—N2	126.05 (13)	C6—C3—H3	109.408
O1—C2—C3	127.51 (13)	C4—C5—H5A	109.473
N2—C2—C3	106.44 (9)	C4—C5—H5B	109.477
N1—C3—C2	101.43 (11)	C4—C5—H5C	109.470
N1—C3—C6	114.97 (9)	H5A—C5—H5B	109.474
C2—C3—C6	111.93 (10)	H5A—C5—H5C	109.461
O2—C4—N1	116.01 (10)	H5B—C5—H5C	109.473
O2—C4—C5	123.27 (12)	C6—C7—H7	119.804
N1—C4—C5	120.71 (13)	C8—C7—H7	119.807
C3—C6—C7	119.42 (11)	C7—C8—H8	120.984
C3—C6—C11	120.67 (13)	C9—C8—H8	120.972
C7—C6—C11	119.82 (12)	C9—C10—H10	121.071
C6—C7—C8	120.39 (14)	C11—C10—H10	121.082
C7—C8—C9	118.04 (17)	C6—C11—H11	119.797
F1—C9—C8	118.03 (16)	C10—C11—H11	119.789
F1—C9—C10	118.50 (14)
C1—N1—C3—C2	−1.25 (11)	O1—C2—C3—C6	−55.41 (16)
C1—N1—C3—C6	−122.21 (10)	N2—C2—C3—N1	0.71 (11)
C3—N1—C1—S1	−178.11 (9)	N2—C2—C3—C6	123.78 (9)
C3—N1—C1—N2	1.32 (11)	N1—C3—C6—C7	−126.90 (11)
C1—N1—C4—O2	−166.54 (10)	N1—C3—C6—C11	56.50 (14)
C1—N1—C4—C5	14.60 (17)	C2—C3—C6—C7	118.06 (11)
C4—N1—C1—S1	−8.49 (18)	C2—C3—C6—C11	−58.54 (12)
C4—N1—C1—N2	170.93 (10)	C3—C6—C7—C8	−175.27 (9)
C3—N1—C4—O2	2.57 (15)	C3—C6—C11—C10	175.46 (9)
C3—N1—C4—C5	−176.29 (9)	C7—C6—C11—C10	−1.12 (16)
C4—N1—C3—C2	−172.31 (9)	C11—C6—C7—C8	1.35 (17)
C4—N1—C3—C6	66.73 (13)	C6—C7—C8—C9	−0.67 (18)
C1—N2—C2—O1	179.24 (10)	C7—C8—C9—F1	179.71 (11)
C1—N2—C2—C3	0.04 (12)	C7—C8—C9—C10	−0.3 (2)
C2—N2—C1—S1	178.64 (9)	F1—C9—C10—C11	−179.49 (10)
C2—N2—C1—N1	−0.83 (12)	C8—C9—C10—C11	0.5 (2)
O1—C2—C3—N1	−178.48 (12)	C9—C10—C11—C6	0.21 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.84 (2)	1.96 (2)	2.7836 (16)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.84 (2)	1.96 (2)	2.7836 (16)	167 (2)

Symmetry code: (i) .