tert-Butyl 2-sulfanylidene-2,3-dihydro-1H-imidazole-1-carboxyl-ate.

In the title mol-ecule, C(8)H(12)N(2)O(2)S, the imidazole ring forms a dihedral angle of 5.9 (2)° with the mean plane of the carboxyl-ate group. In the crystal, mol-ecules are linked by pairs of N-H⋯S hydrogen bonds, forming inversion dimers.

Related literature

The title compound is a mercaptoimidazole derivative. For applications of n class="Chemical">mercaptoimidazole derivatives in the treatment of hyperpigmentation, see: Kasraee (2002 ▶); Kasraee et al. (2005 ▶) and for inhibiting tyrosinase, see: Liao et al. (2012 ▶). For related structures containing inter­molecular N—H⋯S hydrogen bonds, see: Krepps et al. (2001 ▶).

Experimental

Crystal data

C8H12N2O2S

M = 200.26

Monoclinic,

a = 6.8316 (3) Å

b = 8.8893 (5) Å

c = 17.5458 (15) Å

β = 90.789 (6)°

V = 1065.42 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.60 × 0.50 × 0.35 mm

Data collection

Agilent Xcalibur Sapphire3 Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.859, T max = 1.000

4722 measured reflections

2472 independent reflections

1808 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.213

S = 1.09

2472 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.67 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812027924/lh5490sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027924/lh5490Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027924/lh5490Isup3.cml

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

C8H12N2O2S	-
Mr = 200.26	Dx = 1.248 Mg m−3
Monoclinic, P21/c	Melting point: 439 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.8316 (3) Å	Cell parameters from 1507 reflections
b = 8.8893 (5) Å	θ = 3.0–29.2°
c = 17.5458 (15) Å	µ = 0.28 mm−1
β = 90.789 (6)°	T = 293 K
V = 1065.42 (12) Å3	Parallelpiped, colourless
Z = 4	0.60 × 0.50 × 0.35 mm
F(000) = 424

Agilent Xcalibur Sapphire3 Gemini diffractometer	2472 independent reflections
Radiation source: fine-focus sealed tube	1808 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 16.0690 pixels mm-1	θmax = 29.2°, θmin = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→11
Tmin = 0.859, Tmax = 1.000	l = −23→21
4722 measured reflections

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.213	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.120P)2] where P = (Fo2 + 2Fc2)/3
2472 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.67 e Å−3

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
S	0.27124 (9)	0.62848 (7)	0.03744 (6)	0.0726 (4)
O1	0.3738 (3)	0.9165 (2)	0.12448 (15)	0.0823 (8)
O2	0.1365 (3)	1.08602 (18)	0.14513 (10)	0.0541 (5)
N1	−0.1123 (3)	0.6966 (2)	0.03370 (11)	0.0468 (5)
H1A	−0.1457	0.6126	0.0129	0.056*
N2	0.0567 (3)	0.87696 (19)	0.08377 (11)	0.0389 (5)
C1	0.0732 (3)	0.7337 (2)	0.05224 (13)	0.0415 (5)
C2	−0.2421 (3)	0.8086 (3)	0.05181 (14)	0.0508 (6)
H2A	−0.3770	0.8061	0.0440	0.061*
C3	−0.1412 (3)	0.9201 (3)	0.08217 (13)	0.0472 (6)
H3A	−0.1916	1.0109	0.0994	0.057*
C4	0.2096 (3)	0.9595 (3)	0.11969 (14)	0.0469 (6)
C5	0.2572 (4)	1.1899 (3)	0.19323 (15)	0.0587 (7)
C6	0.1128 (6)	1.3169 (4)	0.2072 (2)	0.0962 (12)
H6A	0.0046	1.2795	0.2360	0.144*
H6B	0.0656	1.3553	0.1592	0.144*
H6C	0.1769	1.3960	0.2352	0.144*
C7	0.4278 (5)	1.2477 (4)	0.1471 (2)	0.0896 (11)
H7A	0.5177	1.1669	0.1379	0.134*
H7B	0.4935	1.3264	0.1748	0.134*
H7C	0.3800	1.2865	0.0992	0.134*
C8	0.3180 (8)	1.1119 (4)	0.2653 (2)	0.1084 (15)
H8A	0.4083	1.0327	0.2538	0.163*
H8B	0.2047	1.0702	0.2893	0.163*
H8C	0.3798	1.1829	0.2992	0.163*

	U11	U22	U33	U12	U13	U23
S	0.0365 (4)	0.0442 (5)	0.1370 (8)	−0.0011 (3)	0.0015 (4)	−0.0349 (4)
O1	0.0419 (11)	0.0628 (12)	0.142 (2)	0.0071 (9)	−0.0166 (12)	−0.0510 (13)
O2	0.0475 (10)	0.0450 (9)	0.0696 (11)	0.0052 (8)	−0.0040 (8)	−0.0234 (8)
N1	0.0350 (10)	0.0458 (11)	0.0598 (11)	−0.0064 (9)	0.0021 (8)	−0.0122 (9)
N2	0.0304 (9)	0.0365 (9)	0.0501 (10)	0.0008 (7)	0.0051 (7)	−0.0070 (8)
C1	0.0348 (12)	0.0363 (11)	0.0535 (12)	−0.0065 (9)	0.0045 (9)	−0.0055 (10)
C2	0.0310 (11)	0.0640 (16)	0.0574 (14)	0.0018 (11)	0.0019 (10)	−0.0141 (12)
C3	0.0346 (12)	0.0546 (14)	0.0525 (13)	0.0079 (10)	0.0028 (9)	−0.0103 (11)
C4	0.0383 (12)	0.0404 (12)	0.0622 (14)	0.0022 (10)	0.0011 (10)	−0.0125 (11)
C5	0.0710 (18)	0.0431 (13)	0.0619 (15)	−0.0010 (13)	−0.0053 (13)	−0.0206 (12)
C6	0.104 (3)	0.0696 (19)	0.115 (3)	0.014 (2)	−0.003 (2)	−0.048 (2)
C7	0.090 (2)	0.0680 (19)	0.111 (3)	−0.0256 (19)	0.000 (2)	−0.029 (2)
C8	0.167 (5)	0.082 (3)	0.075 (2)	0.001 (2)	−0.038 (2)	−0.0115 (19)

S—C1	1.668 (2)	C5—C8	1.496 (5)
O1—C4	1.186 (3)	C5—C7	1.518 (4)
O2—C4	1.312 (3)	C5—C6	1.521 (4)
O2—C5	1.492 (3)	C6—H6A	0.9600
N1—C1	1.345 (3)	C6—H6B	0.9600
N1—C2	1.374 (3)	C6—H6C	0.9600
N1—H1A	0.8600	C7—H7A	0.9600
N2—C1	1.394 (3)	C7—H7B	0.9600
N2—C3	1.405 (3)	C7—H7C	0.9600
N2—C4	1.417 (3)	C8—H8A	0.9600
C2—C3	1.316 (3)	C8—H8B	0.9600
C2—H2A	0.9300	C8—H8C	0.9600
C3—H3A	0.9300
C4—O2—C5	120.9 (2)	O2—C5—C6	101.3 (2)
C1—N1—C2	112.04 (19)	C8—C5—C6	112.4 (3)
C1—N1—H1A	124.0	C7—C5—C6	109.8 (3)
C2—N1—H1A	124.0	C5—C6—H6A	109.5
C1—N2—C3	108.91 (18)	C5—C6—H6B	109.5
C1—N2—C4	125.90 (19)	H6A—C6—H6B	109.5
C3—N2—C4	124.82 (19)	C5—C6—H6C	109.5
N1—C1—N2	103.84 (18)	H6A—C6—H6C	109.5
N1—C1—S	126.03 (17)	H6B—C6—H6C	109.5
N2—C1—S	130.11 (16)	C5—C7—H7A	109.5
C3—C2—N1	107.6 (2)	C5—C7—H7B	109.5
C3—C2—H2A	126.2	H7A—C7—H7B	109.5
N1—C2—H2A	126.2	C5—C7—H7C	109.5
C2—C3—N2	107.6 (2)	H7A—C7—H7C	109.5
C2—C3—H3A	126.2	H7B—C7—H7C	109.5
N2—C3—H3A	126.2	C5—C8—H8A	109.5
O1—C4—O2	128.0 (2)	C5—C8—H8B	109.5
O1—C4—N2	123.7 (2)	H8A—C8—H8B	109.5
O2—C4—N2	108.25 (19)	C5—C8—H8C	109.5
O2—C5—C8	109.7 (2)	H8A—C8—H8C	109.5
O2—C5—C7	109.3 (2)	H8B—C8—H8C	109.5
C8—C5—C7	113.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Si	0.86	2.47	3.324 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Si	0.86	2.47	3.324 (2)	174

Symmetry code: (i) .