Literature DB >> 21587626

1-Acetyl-5-isobutyl-2-sulfanylidene-imidazolidin-4-one.

Abstract

There are two independent mol-ecules in the asymmetric unit of the title compound, C(9)H(14)N(2)O(2)S. In the crystal, the mol-ecules are linked by N-H⋯O hydrogen bonds, forming a chain along the a axis.

Entities: CellLine Chemical Disease Species

Year: 2010 PMID： 21587626 PMCID： PMC2983327 DOI： 10.1107/S1600536810037256

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For biological activity of thiohydantoins, see: Lopez & Trigo (1985 ▶). For a related structure, see: Sulbaran et al. (2007 ▶).

Experimental

Crystal data

C9H14N2O2S M = 214.28 Triclinic, a = 7.1856 (8) Å b = 9.7567 (11) Å c = 16.4226 (15) Å α = 101.231 (2)° β = 93.965 (1)° γ = 90.491 (1)° V = 1126.3 (2) Å3 Z = 4 Mo Kα radiation μ = 0.27 mm−1 T = 298 K 0.42 × 0.35 × 0.14 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.897, T max = 0.964 5877 measured reflections 3916 independent reflections 2199 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.054 wR(F 2) = 0.138 S = 1.02 3916 reflections 259 parameters H-atom parameters constrained Δρmax = 0.27 e Å−3 Δρmin = −0.17 e Å−3 Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037256/is2592sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037256/is2592Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₉H₁₄N₂O₂S	Z = 4
M_r = 214.28	F(000) = 456
Triclinic, P1	D_x = 1.264 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1856 (8) Å	Cell parameters from 1409 reflections
b = 9.7567 (11) Å	θ = 2.5–22.5°
c = 16.4226 (15) Å	µ = 0.27 mm⁻¹
α = 101.231 (2)°	T = 298 K
β = 93.965 (1)°	Block, colourless
γ = 90.491 (1)°	0.42 × 0.35 × 0.14 mm
V = 1126.3 (2) Å³

Bruker SMART APEX CCD area-detector diffractometer	3916 independent reflections
Radiation source: fine-focus sealed tube	2199 reflections with I > 2σ(I)
graphite	R_int = 0.023
φ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.897, T_max = 0.964	k = −9→11
5877 measured reflections	l = −18→19

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0539P)² + 0.2948P] where P = (F_o² + 2F_c²)/3
3916 reflections	(Δ/σ)_max = 0.001
259 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.17 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	U_iso*/U_eq
N1	0.3760 (3)	0.2881 (3)	0.16750 (16)	0.0404 (7)
N2	0.0770 (3)	0.2612 (3)	0.18054 (17)	0.0523 (8)
H2	−0.0417	0.2710	0.1746	0.063*
N3	0.0219 (3)	0.7835 (3)	0.17203 (16)	0.0429 (7)
N4	0.3235 (4)	0.7558 (3)	0.18537 (17)	0.0518 (8)
H4	0.4406	0.7664	0.1800	0.062*
O1	0.0752 (3)	0.1110 (3)	0.27212 (17)	0.0746 (8)
O2	0.6815 (3)	0.2536 (3)	0.16880 (16)	0.0638 (7)
O3	0.3503 (3)	0.6072 (3)	0.27747 (17)	0.0748 (8)
O4	−0.2837 (3)	0.7469 (3)	0.17042 (16)	0.0649 (7)
S1	0.13550 (12)	0.41653 (10)	0.06933 (6)	0.0563 (3)
S2	0.23535 (13)	0.90538 (11)	0.07109 (6)	0.0626 (3)
C1	0.2002 (4)	0.3238 (3)	0.13812 (19)	0.0403 (8)
C2	0.1575 (4)	0.1820 (4)	0.2329 (2)	0.0520 (9)
C3	0.3646 (4)	0.2041 (4)	0.2328 (2)	0.0466 (9)
H3	0.4243	0.1141	0.2158	0.056*
C4	0.4495 (5)	0.2774 (4)	0.3174 (2)	0.0569 (10)
H4A	0.5733	0.3121	0.3106	0.068*
H4B	0.3747	0.3576	0.3373	0.068*
C5	0.4652 (6)	0.1881 (4)	0.3833 (2)	0.0698 (11)
H5	0.3394	0.1543	0.3900	0.084*
C6	0.5376 (7)	0.2777 (5)	0.4657 (3)	0.1015 (16)
H6A	0.6642	0.3068	0.4621	0.152*
H6B	0.5328	0.2245	0.5089	0.152*
H6C	0.4616	0.3585	0.4782	0.152*
C7	0.5853 (8)	0.0619 (5)	0.3603 (3)	0.121 (2)
H7A	0.7066	0.0916	0.3486	0.182*
H7B	0.5283	0.0007	0.3119	0.182*
H7C	0.5972	0.0131	0.4058	0.182*
C8	0.5509 (4)	0.3120 (3)	0.1399 (2)	0.0453 (8)
C9	0.5730 (5)	0.4020 (4)	0.0785 (2)	0.0639 (11)
H9A	0.7025	0.4090	0.0686	0.096*
H9B	0.5277	0.4934	0.0996	0.096*
H9C	0.5030	0.3621	0.0273	0.096*
C10	0.1898 (4)	0.8166 (3)	0.1424 (2)	0.0427 (8)
C11	0.2580 (5)	0.6769 (4)	0.2376 (2)	0.0502 (9)
C12	0.0504 (4)	0.6996 (3)	0.2371 (2)	0.0461 (9)
H12	−0.0175	0.6099	0.2202	0.055*
C13	−0.0073 (5)	0.7752 (4)	0.3214 (2)	0.0573 (10)
H13A	0.0745	0.8564	0.3406	0.069*
H13B	−0.1329	0.8086	0.3142	0.069*
C14	−0.0024 (6)	0.6886 (4)	0.3882 (2)	0.0724 (12)
H14	0.1255	0.6567	0.3955	0.087*
C15	−0.1284 (9)	0.5618 (6)	0.3658 (3)	0.126 (2)
H15A	−0.1293	0.5155	0.4122	0.190*
H15B	−0.0840	0.4992	0.3189	0.190*
H15C	−0.2526	0.5894	0.3518	0.190*
C16	−0.0487 (7)	0.7818 (6)	0.4705 (3)	0.1089 (17)
H16A	−0.1747	0.8127	0.4655	0.163*
H16B	0.0352	0.8614	0.4831	0.163*
H16C	−0.0355	0.7296	0.5143	0.163*
C17	−0.1606 (4)	0.8094 (4)	0.1444 (2)	0.0471 (9)
C18	−0.2005 (5)	0.9099 (4)	0.0897 (2)	0.0630 (10)
H18A	−0.3330	0.9169	0.0800	0.094*
H18B	−0.1466	0.8784	0.0376	0.094*
H18C	−0.1478	0.9998	0.1157	0.094*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0242 (14)	0.0472 (17)	0.0518 (16)	0.0029 (11)	0.0067 (12)	0.0132 (14)
N2	0.0207 (14)	0.067 (2)	0.074 (2)	0.0038 (13)	0.0043 (13)	0.0246 (17)
N3	0.0261 (14)	0.0508 (17)	0.0527 (17)	0.0051 (12)	0.0052 (12)	0.0115 (15)
N4	0.0248 (15)	0.0608 (19)	0.074 (2)	0.0033 (13)	0.0075 (14)	0.0212 (17)
O1	0.0495 (16)	0.092 (2)	0.094 (2)	−0.0114 (14)	0.0122 (14)	0.0441 (18)
O2	0.0275 (13)	0.0854 (19)	0.0865 (18)	0.0089 (12)	0.0085 (12)	0.0342 (16)
O3	0.0490 (16)	0.089 (2)	0.098 (2)	0.0208 (14)	0.0066 (14)	0.0459 (18)
O4	0.0317 (13)	0.0777 (18)	0.0915 (19)	0.0010 (12)	0.0099 (13)	0.0299 (16)
S1	0.0400 (5)	0.0709 (7)	0.0607 (6)	0.0080 (4)	−0.0020 (4)	0.0209 (5)
S2	0.0469 (6)	0.0798 (8)	0.0682 (7)	0.0025 (5)	0.0149 (5)	0.0280 (6)
C1	0.0262 (17)	0.044 (2)	0.048 (2)	0.0048 (14)	0.0041 (14)	0.0028 (17)
C2	0.0330 (19)	0.062 (2)	0.065 (2)	−0.0020 (17)	0.0063 (17)	0.020 (2)
C3	0.0324 (18)	0.051 (2)	0.060 (2)	0.0032 (15)	0.0030 (16)	0.0207 (19)
C4	0.044 (2)	0.064 (2)	0.064 (2)	−0.0014 (18)	0.0012 (18)	0.019 (2)
C5	0.064 (3)	0.085 (3)	0.064 (3)	−0.005 (2)	−0.001 (2)	0.026 (2)
C6	0.104 (4)	0.130 (4)	0.068 (3)	−0.016 (3)	−0.008 (3)	0.021 (3)
C7	0.152 (5)	0.109 (4)	0.106 (4)	0.043 (4)	−0.021 (4)	0.037 (4)
C8	0.0260 (18)	0.051 (2)	0.060 (2)	0.0049 (15)	0.0078 (16)	0.0102 (19)
C9	0.042 (2)	0.073 (3)	0.085 (3)	0.0027 (19)	0.0208 (19)	0.031 (2)
C10	0.0293 (18)	0.045 (2)	0.052 (2)	0.0036 (15)	0.0036 (15)	0.0055 (17)
C11	0.036 (2)	0.055 (2)	0.062 (2)	0.0085 (17)	0.0075 (17)	0.016 (2)
C12	0.0333 (18)	0.049 (2)	0.058 (2)	0.0047 (15)	0.0077 (16)	0.0141 (19)
C13	0.049 (2)	0.064 (2)	0.062 (2)	0.0079 (18)	0.0116 (18)	0.016 (2)
C14	0.067 (3)	0.085 (3)	0.072 (3)	0.008 (2)	0.011 (2)	0.028 (3)
C15	0.173 (6)	0.110 (4)	0.108 (4)	−0.037 (4)	0.031 (4)	0.044 (4)
C16	0.115 (4)	0.143 (5)	0.070 (3)	0.022 (4)	0.023 (3)	0.020 (3)
C17	0.0322 (19)	0.051 (2)	0.058 (2)	0.0043 (16)	0.0054 (16)	0.0091 (19)
C18	0.040 (2)	0.072 (3)	0.079 (3)	0.0074 (18)	−0.0009 (19)	0.023 (2)

N1—C1	1.393 (4)	C6—H6B	0.9600
N1—C8	1.398 (4)	C6—H6C	0.9600
N1—C3	1.478 (4)	C7—H7A	0.9600
N2—C2	1.368 (4)	C7—H7B	0.9600
N2—C1	1.372 (4)	C7—H7C	0.9600
N2—H2	0.8600	C8—C9	1.476 (5)
N3—C10	1.390 (4)	C9—H9A	0.9600
N3—C17	1.399 (4)	C9—H9B	0.9600
N3—C12	1.472 (4)	C9—H9C	0.9600
N4—C10	1.361 (4)	C11—C12	1.510 (4)
N4—C11	1.363 (4)	C12—C13	1.524 (4)
N4—H4	0.8600	C12—H12	0.9800
O1—C2	1.209 (4)	C13—C14	1.508 (5)
O2—C8	1.218 (4)	C13—H13A	0.9700
O3—C11	1.205 (4)	C13—H13B	0.9700
O4—C17	1.217 (4)	C14—C15	1.497 (6)
S1—C1	1.626 (3)	C14—C16	1.534 (5)
S2—C10	1.635 (3)	C14—H14	0.9800
C2—C3	1.502 (4)	C15—H15A	0.9600
C3—C4	1.517 (5)	C15—H15B	0.9600
C3—H3	0.9800	C15—H15C	0.9600
C4—C5	1.515 (5)	C16—H16A	0.9600
C4—H4A	0.9700	C16—H16B	0.9600
C4—H4B	0.9700	C16—H16C	0.9600
C5—C7	1.512 (6)	C17—C18	1.471 (5)
C5—C6	1.517 (5)	C18—H18A	0.9600
C5—H5	0.9800	C18—H18B	0.9600
C6—H6A	0.9600	C18—H18C	0.9600

C1—N1—C8	129.4 (3)	C8—C9—H9A	109.5
C1—N1—C3	111.9 (2)	C8—C9—H9B	109.5
C8—N1—C3	118.6 (3)	H9A—C9—H9B	109.5
C2—N2—C1	114.9 (3)	C8—C9—H9C	109.5
C2—N2—H2	122.6	H9A—C9—H9C	109.5
C1—N2—H2	122.6	H9B—C9—H9C	109.5
C10—N3—C17	129.3 (3)	N4—C10—N3	105.3 (3)
C10—N3—C12	111.7 (2)	N4—C10—S2	123.4 (2)
C17—N3—C12	118.8 (3)	N3—C10—S2	131.3 (3)
C10—N4—C11	115.1 (3)	O3—C11—N4	126.2 (3)
C10—N4—H4	122.5	O3—C11—C12	127.9 (3)
C11—N4—H4	122.5	N4—C11—C12	105.9 (3)
N2—C1—N1	104.9 (3)	N3—C12—C11	101.5 (3)
N2—C1—S1	123.4 (2)	N3—C12—C13	112.7 (3)
N1—C1—S1	131.7 (2)	C11—C12—C13	112.0 (3)
O1—C2—N2	125.9 (3)	N3—C12—H12	110.1
O1—C2—C3	127.8 (3)	C11—C12—H12	110.1
N2—C2—C3	106.3 (3)	C13—C12—H12	110.1
N1—C3—C2	101.6 (2)	C14—C13—C12	115.1 (3)
N1—C3—C4	113.5 (3)	C14—C13—H13A	108.5
C2—C3—C4	111.9 (3)	C12—C13—H13A	108.5
N1—C3—H3	109.9	C14—C13—H13B	108.5
C2—C3—H3	109.9	C12—C13—H13B	108.5
C4—C3—H3	109.9	H13A—C13—H13B	107.5
C5—C4—C3	115.3 (3)	C15—C14—C13	112.9 (4)
C5—C4—H4A	108.5	C15—C14—C16	111.7 (4)
C3—C4—H4A	108.5	C13—C14—C16	108.9 (4)
C5—C4—H4B	108.5	C15—C14—H14	107.7
C3—C4—H4B	108.5	C13—C14—H14	107.7
H4A—C4—H4B	107.5	C16—C14—H14	107.7
C7—C5—C4	113.2 (4)	C14—C15—H15A	109.5
C7—C5—C6	110.9 (4)	C14—C15—H15B	109.5
C4—C5—C6	109.3 (3)	H15A—C15—H15B	109.5
C7—C5—H5	107.7	C14—C15—H15C	109.5
C4—C5—H5	107.7	H15A—C15—H15C	109.5
C6—C5—H5	107.7	H15B—C15—H15C	109.5
C5—C6—H6A	109.5	C14—C16—H16A	109.5
C5—C6—H6B	109.5	C14—C16—H16B	109.5
H6A—C6—H6B	109.5	H16A—C16—H16B	109.5
C5—C6—H6C	109.5	C14—C16—H16C	109.5
H6A—C6—H6C	109.5	H16A—C16—H16C	109.5
H6B—C6—H6C	109.5	H16B—C16—H16C	109.5
C5—C7—H7A	109.5	O4—C17—N3	115.9 (3)
C5—C7—H7B	109.5	O4—C17—C18	122.3 (3)
H7A—C7—H7B	109.5	N3—C17—C18	121.7 (3)
C5—C7—H7C	109.5	C17—C18—H18A	109.5
H7A—C7—H7C	109.5	C17—C18—H18B	109.5
H7B—C7—H7C	109.5	H18A—C18—H18B	109.5
O2—C8—N1	116.2 (3)	C17—C18—H18C	109.5
O2—C8—C9	122.6 (3)	H18A—C18—H18C	109.5
N1—C8—C9	121.1 (3)	H18B—C18—H18C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	1.99	2.834 (3)	167
N4—H4···O4ⁱⁱ	0.86	2.01	2.850 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.86	1.99	2.834 (3)	167
N4—H4⋯O4ⁱⁱ	0.86	2.01	2.850 (3)	167

Symmetry codes: (i) ; (ii) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Hydrogen-bonding patterns in rac-1-acetyl-5-methyl-2-thioxoimidazolidin-4-one.

Authors: Maria E Sulbaran; Gerzon E Delgado; Asiloé J Mora; Ali Bahsas; Hector Novoa de Armas; Norbert Blaton
Journal: Acta Crystallogr C Date: 2007-08-17 Impact factor: 1.172

2 in total